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The crystal structures of three products of the reaction of 2-phenyl­phenol and BCl3 have been determined. The structures show intriguing packing patterns and an inter­esting case of pseudosymmetry. In addition, one of the two polymorphs has a primitive monoclinic crystal system, but it is twinned and emulates an ortho­rhom­bic C-centred structure. Tris(biphenyl-2-yl) borate, C36H27BO3, (III), crystallizes with only one mol­ecule in the asymmetric unit. The dihedral angles between the planes of the aromatic rings in the biphenyl moieties are 50.47 (13), 44.95 (13) and 42.60 (13)°. The boron centre is in a trigonal planar coordination with two of the biphenyl residues on one side of the BO3 plane and the remaining biphenyl residue on the other side. One polymorph of 10-oxa-9-boraphenanthren-9-ol, C12H9BO2, (Va), crystallizes with two almost identical mol­ecules (r.m.s. deviation of all non-H atoms = 0.039 Å) in the asymmetric unit. All non-H atoms lie in a common plane (r.m.s. deviation = 0.015 Å for both mol­ecules in the asymmetric unit). The two mol­ecules in the asymmetric unit are connected into dimers via O-H...O hydrogen bonds. A second polymorph of 10-oxa-9-boraphen­anthren-9-ol, (Vb), crystallizes as a pseudo-merohedral twin with two almost identical mol­ecules (r.m.s. deviation of all non-H atoms = 0.035 Å) in the asymmetric unit. All non-H atoms lie in a common plane (r.m.s. deviation = 0.012 Å for mol­ecule 1 and 0.014 Å for mol­ecule A). Each of the two mol­ecules in the asymmetric unit is connected into a centrosymmetric dimer via O-H...O hydrogen bonds. The main difference between the two polymorphic structures is that in (Va) the two mol­ecules in the asymmetric unit are hydrogen bonded to each other, whereas in (Vb), each mol­ecule in the asymmetric unit forms a hydrogen-bonded dimer with its centrosymmetric equivalent. 9-[(Biphenyl-2-yl)­oxy]-10-oxa-9-bora­phen­an­threne, C24H17BO2, (VI), crystallizes with four mol­ecules in the asymmetric unit. The main differences between them are the dihedral angles between the ring planes. Apart from the biphenyl moiety, all non-H atoms lie in a common plane (r.m.s. deviations = 0.026, 0.0231, 0.019 and 0.033 Å for mol­ecules 1, A, B and C, respectively). This structure shows pseudosymmetry; mol­ecules 1 and A, as well as mol­ecules B and C, are related by a pseudo-translation of about 1 \over 2 in the direction of the b axis. Mol­ecules 1 and B, as well as mol­ecules A and C, are related by a pseudo-inversion centre at 1 \over 4,1 \over 8,1 \over 2. Neither between mol­ecules 1 and C nor between mol­ecules A and B can pseudosymmetry be found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961401290X/sk3550sup1.cif
Contains datablocks III, Va, Vb, VI, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550IIIsup2.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550Vasup3.hkl
Contains datablock Va

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550Vbsup4.hkl
Contains datablock Vb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550VIsup5.hkl
Contains datablock VI

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550IIIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550Vasup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550Vbsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550VIsup9.cml
Supplementary material

CCDC references: 1006553; 1006554; 1006555; 1006556

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(III) Tris(biphenyl-2-yl) borate top
Crystal data top
C36H27BO3F(000) = 1088
Mr = 518.39Dx = 1.278 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8174 reflections
a = 13.9098 (17) Åθ = 2.3–27.6°
b = 10.1293 (8) ŵ = 0.08 mm1
c = 19.485 (2) ÅT = 173 K
β = 100.966 (10)°Block, colourless
V = 2695.2 (5) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
3289 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.112
Genix 3D multilayer optics monochromatorθmax = 27.2°, θmin = 2.3°
ω scansh = 1715
15600 measured reflectionsk = 1112
5830 independent reflectionsl = 2524
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0434P)2]
where P = (Fo2 + 2Fc2)/3
5830 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
B10.7260 (2)0.5771 (3)0.63846 (13)0.0235 (6)
O10.81117 (13)0.51654 (18)0.63232 (8)0.0286 (4)
O20.65190 (13)0.58937 (18)0.58340 (8)0.0282 (4)
O30.71597 (13)0.62411 (17)0.70273 (8)0.0283 (4)
C10.83438 (19)0.4751 (3)0.56939 (11)0.0250 (5)
C20.83996 (19)0.5637 (3)0.51576 (12)0.0264 (6)
C30.8710 (2)0.5138 (3)0.45687 (13)0.0314 (6)
H30.87500.57150.41900.038*
C40.8961 (2)0.3831 (3)0.45228 (13)0.0342 (6)
H40.91920.35230.41230.041*
C50.8878 (2)0.2972 (3)0.50529 (13)0.0333 (6)
H50.90340.20640.50170.040*
C60.8563 (2)0.3441 (3)0.56422 (13)0.0306 (6)
H60.84990.28520.60100.037*
C110.8143 (2)0.7056 (3)0.51816 (12)0.0281 (6)
C120.7511 (2)0.7614 (3)0.46223 (13)0.0327 (6)
H120.72470.70810.42300.039*
C130.7259 (2)0.8932 (3)0.46242 (14)0.0390 (7)
H130.68280.93010.42350.047*
C140.7635 (2)0.9714 (3)0.51932 (16)0.0403 (7)
H140.74591.06190.51980.048*
C150.8269 (2)0.9173 (3)0.57546 (15)0.0387 (7)
H150.85310.97100.61450.046*
C160.8523 (2)0.7851 (3)0.57503 (13)0.0326 (6)
H160.89600.74850.61380.039*
C210.56304 (19)0.6449 (3)0.58975 (12)0.0276 (6)
C220.4901 (2)0.5650 (3)0.60773 (12)0.0282 (6)
C230.4000 (2)0.6259 (3)0.60850 (14)0.0363 (7)
H230.34790.57460.61960.044*
C240.3848 (2)0.7583 (3)0.59361 (15)0.0426 (7)
H240.32280.79700.59440.051*
C250.4595 (2)0.8338 (3)0.57768 (15)0.0402 (7)
H250.44960.92520.56800.048*
C260.5491 (2)0.7770 (3)0.57566 (13)0.0347 (6)
H260.60080.82910.56460.042*
C310.5055 (2)0.4246 (3)0.62803 (12)0.0286 (6)
C320.4716 (2)0.3773 (3)0.68588 (14)0.0380 (7)
H320.44080.43680.71260.046*
C330.4812 (3)0.2475 (3)0.70578 (16)0.0485 (8)
H330.45820.21800.74600.058*
C340.5248 (2)0.1600 (3)0.66666 (16)0.0469 (8)
H340.52990.06930.67910.056*
C350.5608 (2)0.2041 (3)0.60975 (15)0.0426 (7)
H350.59210.14400.58370.051*
C360.5516 (2)0.3362 (3)0.59020 (13)0.0355 (7)
H360.57680.36610.55090.043*
C410.7820 (2)0.5872 (3)0.76225 (11)0.0277 (6)
C420.84756 (19)0.6795 (3)0.79779 (12)0.0283 (6)
C430.9119 (2)0.6334 (3)0.85699 (13)0.0369 (7)
H430.95760.69320.88270.044*
C440.9114 (2)0.5051 (3)0.87920 (14)0.0443 (8)
H440.95700.47700.91920.053*
C450.8450 (3)0.4172 (3)0.84366 (14)0.0443 (8)
H450.84400.32850.85930.053*
C460.7796 (2)0.4581 (3)0.78483 (14)0.0381 (7)
H460.73330.39780.76010.046*
C510.8516 (2)0.8196 (3)0.77710 (11)0.0285 (6)
C520.7681 (2)0.8952 (3)0.75813 (14)0.0359 (7)
H520.70570.85440.75340.043*
C530.7737 (2)1.0292 (3)0.74593 (15)0.0414 (7)
H530.71551.07980.73380.050*
C540.8635 (3)1.0894 (3)0.75137 (14)0.0428 (7)
H540.86741.18150.74290.051*
C550.9477 (2)1.0158 (3)0.76907 (14)0.0426 (8)
H551.00981.05700.77230.051*
C560.9422 (2)0.8822 (3)0.78214 (12)0.0367 (7)
H561.00070.83220.79470.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0253 (16)0.0214 (14)0.0248 (13)0.0017 (12)0.0072 (11)0.0017 (11)
O10.0286 (10)0.0367 (10)0.0212 (8)0.0045 (9)0.0067 (7)0.0003 (7)
O20.0216 (10)0.0364 (10)0.0273 (8)0.0005 (8)0.0066 (7)0.0018 (7)
O30.0285 (10)0.0322 (10)0.0247 (8)0.0057 (8)0.0065 (7)0.0007 (7)
C10.0200 (13)0.0327 (14)0.0215 (11)0.0048 (11)0.0017 (10)0.0041 (10)
C20.0209 (14)0.0346 (15)0.0231 (11)0.0015 (11)0.0023 (10)0.0022 (10)
C30.0319 (16)0.0358 (16)0.0280 (13)0.0050 (13)0.0094 (11)0.0015 (11)
C40.0310 (16)0.0433 (17)0.0298 (13)0.0011 (13)0.0097 (11)0.0102 (12)
C50.0322 (16)0.0291 (14)0.0378 (14)0.0032 (13)0.0049 (12)0.0061 (11)
C60.0299 (16)0.0330 (16)0.0282 (12)0.0022 (12)0.0035 (11)0.0029 (10)
C110.0278 (15)0.0298 (14)0.0290 (12)0.0036 (12)0.0113 (10)0.0001 (10)
C120.0345 (16)0.0367 (16)0.0287 (13)0.0036 (13)0.0107 (11)0.0026 (11)
C130.0366 (17)0.0399 (17)0.0432 (15)0.0013 (14)0.0145 (13)0.0109 (13)
C140.0416 (19)0.0291 (15)0.0564 (18)0.0017 (14)0.0250 (14)0.0040 (13)
C150.0373 (18)0.0342 (16)0.0473 (16)0.0071 (14)0.0150 (13)0.0083 (13)
C160.0297 (16)0.0355 (16)0.0335 (13)0.0037 (13)0.0083 (11)0.0004 (11)
C210.0222 (14)0.0370 (16)0.0235 (11)0.0014 (12)0.0039 (10)0.0028 (10)
C220.0202 (13)0.0371 (15)0.0273 (12)0.0016 (12)0.0050 (10)0.0058 (10)
C230.0261 (16)0.0433 (17)0.0410 (14)0.0029 (13)0.0103 (12)0.0005 (13)
C240.0309 (17)0.0491 (19)0.0482 (17)0.0117 (15)0.0086 (13)0.0001 (14)
C250.0391 (18)0.0340 (16)0.0476 (16)0.0089 (14)0.0085 (13)0.0003 (13)
C260.0338 (17)0.0347 (16)0.0356 (14)0.0042 (13)0.0069 (12)0.0022 (11)
C310.0223 (14)0.0352 (15)0.0263 (12)0.0047 (12)0.0003 (10)0.0009 (10)
C320.0366 (17)0.0427 (17)0.0373 (14)0.0053 (14)0.0133 (12)0.0007 (13)
C330.048 (2)0.057 (2)0.0422 (16)0.0020 (17)0.0121 (14)0.0145 (14)
C340.051 (2)0.0377 (17)0.0491 (17)0.0017 (15)0.0034 (15)0.0119 (14)
C350.047 (2)0.0377 (17)0.0432 (16)0.0078 (15)0.0089 (13)0.0003 (13)
C360.0382 (17)0.0404 (17)0.0281 (13)0.0009 (14)0.0070 (11)0.0006 (11)
C410.0278 (15)0.0364 (15)0.0208 (11)0.0055 (12)0.0089 (10)0.0012 (10)
C420.0257 (15)0.0406 (16)0.0208 (11)0.0038 (12)0.0099 (10)0.0034 (10)
C430.0288 (16)0.0565 (19)0.0256 (12)0.0055 (14)0.0054 (11)0.0004 (12)
C440.0403 (18)0.070 (2)0.0236 (13)0.0179 (17)0.0091 (12)0.0125 (14)
C450.060 (2)0.0415 (17)0.0354 (14)0.0172 (17)0.0191 (14)0.0124 (13)
C460.0466 (19)0.0382 (17)0.0325 (14)0.0065 (14)0.0152 (13)0.0012 (12)
C510.0247 (14)0.0416 (16)0.0198 (11)0.0027 (12)0.0058 (10)0.0031 (10)
C520.0252 (16)0.0403 (17)0.0431 (15)0.0001 (13)0.0088 (12)0.0043 (12)
C530.0380 (19)0.0376 (17)0.0493 (17)0.0022 (14)0.0102 (14)0.0042 (13)
C540.052 (2)0.0403 (17)0.0380 (15)0.0095 (16)0.0135 (14)0.0055 (13)
C550.0365 (18)0.059 (2)0.0343 (14)0.0188 (16)0.0109 (12)0.0041 (13)
C560.0276 (16)0.0546 (19)0.0279 (13)0.0038 (14)0.0050 (11)0.0006 (12)
Geometric parameters (Å, º) top
B1—O21.345 (3)C25—C261.379 (4)
B1—O11.359 (4)C25—H250.9500
B1—O31.372 (3)C26—H260.9500
O1—C11.391 (3)C31—C321.388 (4)
O2—C211.385 (3)C31—C361.391 (4)
O3—C411.387 (3)C32—C331.370 (4)
C1—C61.370 (4)C32—H320.9500
C1—C21.391 (4)C33—C341.382 (5)
C2—C31.396 (4)C33—H330.9500
C2—C111.483 (4)C34—C351.375 (4)
C3—C41.377 (4)C34—H340.9500
C3—H30.9500C35—C361.390 (4)
C4—C51.372 (4)C35—H350.9500
C4—H40.9500C36—H360.9500
C5—C61.389 (4)C41—C461.381 (4)
C5—H50.9500C41—C421.395 (4)
C6—H60.9500C42—C431.399 (4)
C11—C121.384 (4)C42—C511.480 (4)
C11—C161.390 (4)C43—C441.370 (5)
C12—C131.380 (4)C43—H430.9500
C12—H120.9500C44—C451.371 (5)
C13—C141.382 (4)C44—H440.9500
C13—H130.9500C45—C461.385 (4)
C14—C151.380 (4)C45—H450.9500
C14—H140.9500C46—H460.9500
C15—C161.386 (4)C51—C521.381 (4)
C15—H150.9500C51—C561.397 (4)
C16—H160.9500C52—C531.383 (4)
C21—C261.373 (4)C52—H520.9500
C21—C221.393 (4)C53—C541.376 (5)
C22—C231.399 (4)C53—H530.9500
C22—C311.481 (4)C54—C551.376 (5)
C23—C241.380 (4)C54—H540.9500
C23—H230.9500C55—C561.383 (4)
C24—C251.373 (4)C55—H550.9500
C24—H240.9500C56—H560.9500
O2—B1—O1121.3 (2)C21—C26—C25119.7 (3)
O2—B1—O3120.0 (2)C21—C26—H26120.2
O1—B1—O3118.6 (2)C25—C26—H26120.2
B1—O1—C1124.47 (19)C32—C31—C36118.0 (3)
B1—O2—C21121.87 (19)C32—C31—C22119.6 (3)
B1—O3—C41120.3 (2)C36—C31—C22122.3 (2)
C6—C1—C2121.7 (2)C33—C32—C31122.1 (3)
C6—C1—O1116.7 (2)C33—C32—H32118.9
C2—C1—O1121.6 (2)C31—C32—H32118.9
C1—C2—C3117.0 (2)C32—C33—C34119.2 (3)
C1—C2—C11123.6 (2)C32—C33—H33120.4
C3—C2—C11119.4 (2)C34—C33—H33120.4
C4—C3—C2121.6 (2)C35—C34—C33120.1 (3)
C4—C3—H3119.2C35—C34—H34119.9
C2—C3—H3119.2C33—C34—H34119.9
C5—C4—C3120.2 (2)C34—C35—C36120.3 (3)
C5—C4—H4119.9C34—C35—H35119.8
C3—C4—H4119.9C36—C35—H35119.8
C4—C5—C6119.4 (3)C35—C36—C31120.1 (3)
C4—C5—H5120.3C35—C36—H36119.9
C6—C5—H5120.3C31—C36—H36119.9
C1—C6—C5120.1 (2)C46—C41—O3118.0 (2)
C1—C6—H6119.9C46—C41—C42121.9 (2)
C5—C6—H6119.9O3—C41—C42120.0 (2)
C12—C11—C16118.6 (2)C41—C42—C43116.2 (3)
C12—C11—C2119.4 (2)C41—C42—C51124.3 (2)
C16—C11—C2121.9 (2)C43—C42—C51119.6 (2)
C13—C12—C11121.1 (3)C44—C43—C42122.4 (3)
C13—C12—H12119.5C44—C43—H43118.8
C11—C12—H12119.5C42—C43—H43118.8
C12—C13—C14119.9 (3)C43—C44—C45120.0 (3)
C12—C13—H13120.0C43—C44—H44120.0
C14—C13—H13120.0C45—C44—H44120.0
C15—C14—C13119.7 (3)C44—C45—C46119.8 (3)
C15—C14—H14120.1C44—C45—H45120.1
C13—C14—H14120.1C46—C45—H45120.1
C14—C15—C16120.3 (3)C41—C46—C45119.7 (3)
C14—C15—H15119.9C41—C46—H46120.2
C16—C15—H15119.9C45—C46—H46120.2
C15—C16—C11120.4 (3)C52—C51—C56118.0 (3)
C15—C16—H16119.8C52—C51—C42122.1 (3)
C11—C16—H16119.8C56—C51—C42119.8 (3)
C26—C21—O2118.2 (3)C51—C52—C53121.2 (3)
C26—C21—C22122.3 (3)C51—C52—H52119.4
O2—C21—C22119.5 (2)C53—C52—H52119.4
C21—C22—C23116.3 (3)C54—C53—C52120.1 (3)
C21—C22—C31123.3 (2)C54—C53—H53119.9
C23—C22—C31120.3 (3)C52—C53—H53119.9
C24—C23—C22121.8 (3)C53—C54—C55119.8 (3)
C24—C23—H23119.1C53—C54—H54120.1
C22—C23—H23119.1C55—C54—H54120.1
C25—C24—C23119.8 (3)C54—C55—C56120.2 (3)
C25—C24—H24120.1C54—C55—H55119.9
C23—C24—H24120.1C56—C55—H55119.9
C24—C25—C26120.0 (3)C55—C56—C51120.8 (3)
C24—C25—H25120.0C55—C56—H56119.6
C26—C25—H25120.0C51—C56—H56119.6
O2—B1—O1—C17.2 (4)O2—C21—C26—C25176.4 (2)
O3—B1—O1—C1174.0 (2)C22—C21—C26—C251.4 (4)
O1—B1—O2—C21176.7 (2)C24—C25—C26—C210.1 (4)
O3—B1—O2—C212.2 (4)C21—C22—C31—C32134.5 (3)
O2—B1—O3—C41165.8 (2)C23—C22—C31—C3242.9 (3)
O1—B1—O3—C4113.0 (4)C21—C22—C31—C3646.7 (4)
B1—O1—C1—C6122.8 (3)C23—C22—C31—C36135.8 (3)
B1—O1—C1—C260.4 (3)C36—C31—C32—C330.8 (4)
C6—C1—C2—C31.4 (4)C22—C31—C32—C33178.0 (3)
O1—C1—C2—C3175.2 (2)C31—C32—C33—C340.9 (5)
C6—C1—C2—C11178.2 (2)C32—C33—C34—C352.1 (5)
O1—C1—C2—C115.2 (4)C33—C34—C35—C361.5 (5)
C1—C2—C3—C40.7 (4)C34—C35—C36—C310.2 (4)
C11—C2—C3—C4179.7 (3)C32—C31—C36—C351.3 (4)
C2—C3—C4—C52.2 (4)C22—C31—C36—C35177.4 (3)
C3—C4—C5—C61.6 (4)B1—O3—C41—C4670.0 (3)
C2—C1—C6—C52.0 (4)B1—O3—C41—C42110.6 (3)
O1—C1—C6—C5174.8 (2)C46—C41—C42—C431.0 (4)
C4—C5—C6—C10.4 (4)O3—C41—C42—C43179.6 (2)
C1—C2—C11—C12129.9 (3)C46—C41—C42—C51178.3 (3)
C3—C2—C11—C1249.7 (4)O3—C41—C42—C511.1 (4)
C1—C2—C11—C1650.4 (4)C41—C42—C43—C440.2 (4)
C3—C2—C11—C16130.0 (3)C51—C42—C43—C44179.5 (3)
C16—C11—C12—C130.0 (4)C42—C43—C44—C451.1 (5)
C2—C11—C12—C13179.7 (3)C43—C44—C45—C460.8 (5)
C11—C12—C13—C140.4 (4)O3—C41—C46—C45179.3 (3)
C12—C13—C14—C150.6 (5)C42—C41—C46—C451.2 (4)
C13—C14—C15—C160.3 (5)C44—C45—C46—C410.3 (5)
C14—C15—C16—C110.1 (4)C41—C42—C51—C5244.7 (4)
C12—C11—C16—C150.2 (4)C43—C42—C51—C52134.6 (3)
C2—C11—C16—C15179.9 (3)C41—C42—C51—C56140.7 (3)
B1—O2—C21—C2694.4 (3)C43—C42—C51—C5640.0 (3)
B1—O2—C21—C2287.7 (3)C56—C51—C52—C531.4 (4)
C26—C21—C22—C232.0 (3)C42—C51—C52—C53173.3 (2)
O2—C21—C22—C23175.7 (2)C51—C52—C53—C541.2 (4)
C26—C21—C22—C31175.5 (2)C52—C53—C54—C550.1 (4)
O2—C21—C22—C316.7 (3)C53—C54—C55—C560.7 (4)
C21—C22—C23—C241.2 (4)C54—C55—C56—C510.5 (4)
C31—C22—C23—C24176.4 (2)C52—C51—C56—C550.5 (4)
C22—C23—C24—C250.2 (4)C42—C51—C56—C55174.2 (2)
C23—C24—C25—C260.9 (4)
(Va) 10-oxa-9-boraphenanthren-9-ol top
Crystal data top
C12H9BO2F(000) = 816
Mr = 196.00Dx = 1.394 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 7034 reflections
a = 14.7548 (11) Åθ = 2.2–25.5°
b = 5.1497 (3) ŵ = 0.09 mm1
c = 24.580 (2) ÅT = 173 K
V = 1867.7 (2) Å3Plate, colourless
Z = 80.26 × 0.14 × 0.08 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.105
Graphite monochromatorθmax = 25.1°, θmin = 2.8°
ω scansh = 1717
10071 measured reflectionsk = 65
1687 independent reflectionsl = 2929
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0533P)2]
where P = (Fo2 + 2Fc2)/3
1687 reflections(Δ/σ)max = 0.013
279 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.21 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
B10.3167 (4)0.6824 (12)0.0409 (2)0.0337 (11)
O10.3872 (2)0.8313 (7)0.06190 (12)0.0363 (7)
O20.2889 (3)0.7362 (6)0.01058 (19)0.0388 (11)
H20.313 (6)0.886 (17)0.027 (3)0.12 (3)*
C10.2756 (3)0.4643 (8)0.07573 (17)0.0337 (9)
C20.3124 (3)0.4178 (8)0.12725 (18)0.0336 (10)
C30.2758 (4)0.2209 (9)0.1603 (3)0.0371 (14)
H30.29970.19040.19560.044*
C40.2045 (3)0.0715 (9)0.1407 (2)0.0449 (11)
H40.18010.06240.16290.054*
C50.1683 (3)0.1147 (8)0.0893 (2)0.0417 (10)
H50.11960.01050.07650.050*
C60.2033 (4)0.3093 (10)0.0567 (3)0.0411 (12)
H60.17870.33870.02160.049*
C110.4220 (5)0.7813 (9)0.1138 (2)0.0334 (14)
C120.3889 (3)0.5825 (9)0.14614 (16)0.0330 (10)
C130.4301 (3)0.5506 (9)0.19729 (18)0.0372 (10)
H130.41050.41460.22060.045*
C140.4981 (5)0.7124 (11)0.2140 (3)0.0420 (14)
H140.52360.68980.24920.050*
C150.5305 (3)0.9072 (9)0.1810 (2)0.0427 (11)
H150.57811.01690.19310.051*
C160.4927 (3)0.9417 (9)0.12993 (19)0.0376 (10)
H160.51491.07300.10630.045*
B1A0.5639 (4)0.6762 (12)0.4560 (2)0.0351 (11)
O1A0.6351 (2)0.8215 (7)0.43636 (12)0.0343 (7)
O2A0.5316 (3)0.7246 (7)0.50612 (18)0.0429 (12)
H2A0.558 (4)0.872 (13)0.523 (2)0.065 (18)*
C1A0.5252 (3)0.4558 (8)0.41985 (18)0.0331 (9)
C2A0.5651 (3)0.4137 (8)0.36860 (18)0.0322 (9)
C3A0.5300 (5)0.2148 (9)0.3357 (3)0.0392 (14)
H3A0.55590.18410.30090.047*
C4A0.4585 (3)0.0635 (9)0.35299 (18)0.0400 (11)
H4A0.43610.07100.33020.048*
C5A0.4188 (3)0.1056 (8)0.40336 (19)0.0403 (11)
H5A0.36920.00200.41500.048*
C6A0.4522 (4)0.2991 (10)0.4363 (2)0.0364 (11)
H6A0.42530.32760.47090.044*
C11A0.6731 (4)0.7762 (8)0.3863 (2)0.0296 (13)
C12A0.6414 (3)0.5792 (9)0.35176 (16)0.0317 (9)
C13A0.6852 (3)0.5554 (8)0.30117 (18)0.0365 (10)
H13A0.66640.42130.27720.044*
C14A0.7556 (5)0.7212 (9)0.2846 (3)0.0393 (14)
H14A0.78320.70200.24990.047*
C15A0.7837 (3)0.9139 (8)0.32028 (18)0.0376 (10)
H15A0.83121.02810.31000.045*
C16A0.7432 (3)0.9414 (9)0.37077 (18)0.0369 (10)
H16A0.76321.07350.39490.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.034 (3)0.034 (2)0.033 (3)0.002 (3)0.004 (2)0.001 (3)
O10.0390 (19)0.0330 (16)0.0368 (17)0.0034 (17)0.0002 (14)0.0049 (16)
O20.039 (2)0.038 (2)0.039 (2)0.0065 (13)0.0033 (19)0.0063 (13)
C10.030 (2)0.032 (2)0.039 (2)0.0048 (18)0.0036 (17)0.0018 (17)
C20.028 (2)0.031 (2)0.042 (3)0.0044 (18)0.0076 (19)0.0033 (18)
C30.028 (3)0.043 (3)0.040 (3)0.003 (2)0.004 (2)0.005 (2)
C40.040 (3)0.039 (3)0.055 (3)0.002 (2)0.012 (2)0.007 (2)
C50.034 (2)0.035 (3)0.057 (3)0.002 (2)0.005 (2)0.001 (2)
C60.035 (3)0.037 (2)0.051 (3)0.000 (3)0.006 (2)0.004 (3)
C110.031 (3)0.036 (3)0.033 (3)0.006 (2)0.001 (2)0.001 (2)
C120.031 (2)0.033 (2)0.035 (2)0.0069 (18)0.0032 (18)0.0010 (19)
C130.033 (2)0.039 (3)0.040 (3)0.0081 (18)0.0046 (18)0.0040 (19)
C140.033 (3)0.056 (3)0.037 (3)0.004 (2)0.005 (2)0.002 (3)
C150.031 (2)0.041 (3)0.056 (3)0.003 (2)0.005 (2)0.007 (2)
C160.032 (2)0.033 (2)0.047 (3)0.0010 (18)0.003 (2)0.0026 (19)
B1A0.031 (3)0.034 (3)0.041 (3)0.004 (3)0.001 (2)0.004 (3)
O1A0.0306 (17)0.0369 (16)0.0354 (17)0.0011 (16)0.0000 (13)0.0046 (16)
O2A0.047 (3)0.043 (2)0.038 (2)0.0107 (16)0.0060 (19)0.0089 (15)
C1A0.028 (2)0.031 (2)0.040 (2)0.0002 (18)0.0033 (18)0.0011 (17)
C2A0.026 (2)0.032 (2)0.038 (2)0.0029 (17)0.0042 (18)0.0020 (18)
C3A0.039 (4)0.035 (3)0.043 (3)0.001 (2)0.007 (3)0.007 (2)
C4A0.035 (3)0.034 (2)0.051 (3)0.0016 (18)0.0104 (19)0.0058 (19)
C5A0.029 (2)0.036 (2)0.056 (3)0.0029 (19)0.005 (2)0.001 (2)
C6A0.031 (3)0.038 (2)0.040 (3)0.001 (2)0.004 (2)0.004 (2)
C11A0.024 (3)0.034 (3)0.031 (3)0.0034 (17)0.006 (2)0.0043 (18)
C12A0.028 (2)0.030 (2)0.037 (2)0.0028 (17)0.0031 (17)0.0032 (18)
C13A0.035 (2)0.035 (3)0.039 (2)0.0027 (18)0.0020 (17)0.0081 (18)
C14A0.035 (3)0.038 (3)0.045 (3)0.004 (2)0.004 (3)0.006 (2)
C15A0.032 (2)0.035 (2)0.046 (2)0.0041 (17)0.0001 (19)0.0033 (19)
C16A0.027 (2)0.038 (3)0.045 (3)0.0011 (18)0.005 (2)0.0066 (18)
Geometric parameters (Å, º) top
B1—O21.360 (7)B1A—O2A1.344 (7)
B1—O11.391 (7)B1A—O1A1.377 (7)
B1—C11.537 (7)B1A—C1A1.550 (7)
O1—C111.400 (7)O1A—C11A1.373 (7)
O2—H20.94 (9)O2A—H2A0.96 (6)
C1—C21.399 (6)C1A—C6A1.405 (7)
C1—C61.411 (7)C1A—C2A1.407 (6)
C2—C31.407 (7)C2A—C3A1.404 (7)
C2—C121.485 (6)C2A—C12A1.472 (6)
C3—C41.389 (8)C3A—C4A1.380 (8)
C3—H30.9500C3A—H3A0.9500
C4—C51.391 (7)C4A—C5A1.386 (6)
C4—H40.9500C4A—H4A0.9500
C5—C61.382 (7)C5A—C6A1.374 (7)
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C11—C121.385 (7)C11A—C16A1.392 (7)
C11—C161.388 (7)C11A—C12A1.402 (7)
C12—C131.406 (6)C12A—C13A1.407 (6)
C13—C141.368 (8)C13A—C14A1.405 (8)
C13—H130.9500C13A—H13A0.9500
C14—C151.376 (8)C14A—C15A1.387 (8)
C14—H140.9500C14A—H14A0.9500
C15—C161.384 (7)C15A—C16A1.385 (6)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
O2—B1—O1117.3 (5)O2A—B1A—O1A119.4 (5)
O2—B1—C1123.2 (5)O2A—B1A—C1A122.0 (5)
O1—B1—C1119.5 (4)O1A—B1A—C1A118.5 (4)
B1—O1—C11120.7 (4)C11A—O1A—B1A122.3 (4)
B1—O2—H2117 (5)B1A—O2A—H2A114 (3)
C2—C1—C6119.8 (4)C6A—C1A—C2A119.3 (4)
C2—C1—B1118.4 (4)C6A—C1A—B1A122.6 (4)
C6—C1—B1121.9 (4)C2A—C1A—B1A118.2 (4)
C1—C2—C3119.8 (5)C3A—C2A—C1A118.3 (5)
C1—C2—C12118.7 (4)C3A—C2A—C12A122.8 (5)
C3—C2—C12121.5 (4)C1A—C2A—C12A118.8 (4)
C4—C3—C2119.3 (6)C4A—C3A—C2A121.0 (6)
C4—C3—H3120.3C4A—C3A—H3A119.5
C2—C3—H3120.3C2A—C3A—H3A119.5
C3—C4—C5121.2 (5)C3A—C4A—C5A120.7 (5)
C3—C4—H4119.4C3A—C4A—H4A119.7
C5—C4—H4119.4C5A—C4A—H4A119.7
C6—C5—C4119.9 (4)C6A—C5A—C4A119.2 (4)
C6—C5—H5120.1C6A—C5A—H5A120.4
C4—C5—H5120.1C4A—C5A—H5A120.4
C5—C6—C1120.1 (5)C5A—C6A—C1A121.5 (5)
C5—C6—H6120.0C5A—C6A—H6A119.3
C1—C6—H6120.0C1A—C6A—H6A119.3
C12—C11—C16122.8 (5)O1A—C11A—C16A116.4 (4)
C12—C11—O1122.0 (5)O1A—C11A—C12A122.0 (5)
C16—C11—O1115.2 (5)C16A—C11A—C12A121.6 (5)
C11—C12—C13116.5 (4)C11A—C12A—C13A116.4 (4)
C11—C12—C2120.7 (4)C11A—C12A—C2A120.2 (4)
C13—C12—C2122.8 (4)C13A—C12A—C2A123.3 (4)
C14—C13—C12121.0 (5)C14A—C13A—C12A122.9 (5)
C14—C13—H13119.5C14A—C13A—H13A118.6
C12—C13—H13119.5C12A—C13A—H13A118.6
C13—C14—C15121.4 (6)C15A—C14A—C13A118.2 (6)
C13—C14—H14119.3C15A—C14A—H14A120.9
C15—C14—H14119.3C13A—C14A—H14A120.9
C14—C15—C16119.3 (5)C16A—C15A—C14A120.7 (5)
C14—C15—H15120.4C16A—C15A—H15A119.6
C16—C15—H15120.4C14A—C15A—H15A119.6
C15—C16—C11119.0 (4)C15A—C16A—C11A120.2 (4)
C15—C16—H16120.5C15A—C16A—H16A119.9
C11—C16—H16120.5C11A—C16A—H16A119.9
O2—B1—O1—C11177.6 (5)O2A—B1A—O1A—C11A177.8 (5)
C1—B1—O1—C111.2 (7)C1A—B1A—O1A—C11A0.6 (7)
O2—B1—C1—C2177.0 (5)O2A—B1A—C1A—C6A2.3 (8)
O1—B1—C1—C21.8 (7)O1A—B1A—C1A—C6A179.4 (4)
O2—B1—C1—C62.0 (8)O2A—B1A—C1A—C2A178.0 (4)
O1—B1—C1—C6179.3 (4)O1A—B1A—C1A—C2A0.3 (7)
C6—C1—C2—C31.5 (6)C6A—C1A—C2A—C3A0.1 (6)
B1—C1—C2—C3179.5 (5)B1A—C1A—C2A—C3A179.8 (5)
C6—C1—C2—C12179.6 (4)C6A—C1A—C2A—C12A179.9 (4)
B1—C1—C2—C120.6 (6)B1A—C1A—C2A—C12A0.2 (6)
C1—C2—C3—C41.3 (7)C1A—C2A—C3A—C4A0.2 (8)
C12—C2—C3—C4179.8 (4)C12A—C2A—C3A—C4A179.8 (4)
C2—C3—C4—C50.5 (8)C2A—C3A—C4A—C5A0.6 (8)
C3—C4—C5—C60.1 (7)C3A—C4A—C5A—C6A0.6 (7)
C4—C5—C6—C10.1 (7)C4A—C5A—C6A—C1A0.3 (7)
C2—C1—C6—C50.9 (7)C2A—C1A—C6A—C5A0.0 (7)
B1—C1—C6—C5179.8 (5)B1A—C1A—C6A—C5A179.7 (5)
B1—O1—C11—C120.6 (7)B1A—O1A—C11A—C16A178.5 (4)
B1—O1—C11—C16179.4 (4)B1A—O1A—C11A—C12A0.3 (7)
C16—C11—C12—C130.7 (7)O1A—C11A—C12A—C13A179.0 (4)
O1—C11—C12—C13179.4 (4)C16A—C11A—C12A—C13A1.0 (7)
C16—C11—C12—C2179.4 (4)O1A—C11A—C12A—C2A0.2 (7)
O1—C11—C12—C21.9 (7)C16A—C11A—C12A—C2A177.8 (4)
C1—C2—C12—C111.2 (6)C3A—C2A—C12A—C11A179.5 (5)
C3—C2—C12—C11177.7 (5)C1A—C2A—C12A—C11A0.4 (6)
C1—C2—C12—C13179.9 (4)C3A—C2A—C12A—C13A0.8 (7)
C3—C2—C12—C130.9 (6)C1A—C2A—C12A—C13A179.2 (4)
C11—C12—C13—C141.2 (7)C11A—C12A—C13A—C14A1.4 (7)
C2—C12—C13—C14177.5 (5)C2A—C12A—C13A—C14A177.3 (5)
C12—C13—C14—C151.8 (8)C12A—C13A—C14A—C15A1.0 (8)
C13—C14—C15—C160.6 (9)C13A—C14A—C15A—C16A0.1 (8)
C14—C15—C16—C111.2 (7)C14A—C15A—C16A—C11A0.3 (7)
C12—C11—C16—C151.8 (8)O1A—C11A—C16A—C15A178.3 (4)
O1—C11—C16—C15179.3 (4)C12A—C11A—C16A—C15A0.1 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1Ai0.94 (9)1.92 (9)2.854 (5)177 (7)
O2A—H2A···O1ii0.96 (6)1.97 (7)2.923 (5)178 (5)
Symmetry codes: (i) x+1, y+2, z1/2; (ii) x+1, y+2, z+1/2.
(Vb) 10-oxa-9-boraphenanthren-9-ol top
Crystal data top
C12H9BO2F(000) = 816
Mr = 196.00Dx = 1.390 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11092 reflections
a = 25.627 (3) Åθ = 2.8–25.8°
b = 5.1594 (4) ŵ = 0.09 mm1
c = 14.7701 (12) ÅT = 173 K
β = 106.459 (7)°Plate, colourless
V = 1872.9 (3) Å30.32 × 0.24 × 0.13 mm
Z = 8
Data collection top
Stoe IPDS II two-circle
diffractometer
2446 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.092
Graphite monochromatorθmax = 25.4°, θmin = 0.8°
ω scansh = 3028
14607 measured reflectionsk = 66
3334 independent reflectionsl = 1715
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.091Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1752P)2]
where P = (Fo2 + 2Fc2)/3
3334 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
B10.45822 (18)0.3199 (8)0.4191 (4)0.0531 (11)
O10.43671 (11)0.1732 (5)0.4786 (2)0.0544 (7)
O20.50917 (11)0.2669 (5)0.4148 (3)0.0611 (8)
H20.51920.12300.44050.092*
C10.42282 (16)0.5375 (7)0.3600 (3)0.0527 (9)
C20.37066 (15)0.5817 (7)0.3721 (3)0.0488 (9)
C30.33857 (17)0.7773 (7)0.3192 (3)0.0540 (10)
H30.30320.80700.32560.065*
C40.35693 (18)0.9279 (7)0.2581 (3)0.0604 (11)
H40.33441.06160.22360.073*
C50.40872 (19)0.8862 (7)0.2460 (3)0.0612 (11)
H50.42120.99040.20330.073*
C60.44123 (18)0.6927 (8)0.2967 (3)0.0585 (10)
H60.47630.66360.28900.070*
C110.38517 (15)0.2231 (7)0.4881 (3)0.0484 (9)
C120.35141 (15)0.4207 (6)0.4378 (3)0.0487 (9)
C130.30071 (16)0.4488 (7)0.4554 (3)0.0545 (10)
H130.27740.58510.42470.065*
C140.28315 (17)0.2885 (8)0.5149 (3)0.0566 (10)
H140.24780.30970.52250.068*
C150.31741 (18)0.0950 (7)0.5642 (3)0.0595 (10)
H150.30590.01420.60670.071*
C160.36872 (18)0.0621 (7)0.5508 (3)0.0561 (10)
H160.39240.06940.58430.067*
B1A0.04310 (17)0.3219 (8)0.4624 (3)0.0490 (10)
O1A0.06230 (10)0.1745 (5)0.54320 (19)0.0487 (7)
O2A0.00752 (10)0.2676 (5)0.4058 (2)0.0541 (7)
H2A0.01960.13500.42590.081*
C1A0.07900 (15)0.5410 (6)0.4415 (3)0.0469 (8)
C2A0.13036 (16)0.5858 (6)0.5072 (3)0.0475 (9)
C3A0.16333 (16)0.7824 (7)0.4894 (3)0.0487 (9)
H3A0.19810.81230.53260.058*
C4A0.14571 (17)0.9360 (7)0.4088 (3)0.0542 (10)
H4A0.16831.07150.39780.065*
C5A0.09572 (17)0.8918 (7)0.3451 (3)0.0554 (10)
H5A0.08410.99580.28990.066*
C6A0.06233 (16)0.6974 (7)0.3607 (3)0.0529 (9)
H6A0.02780.66930.31650.063*
C11A0.11276 (14)0.2229 (6)0.6064 (3)0.0429 (9)
C12A0.14670 (14)0.4190 (6)0.5919 (3)0.0437 (8)
C13A0.19703 (16)0.4449 (7)0.6611 (3)0.0513 (9)
H13A0.22090.58010.65490.062*
C14A0.21292 (16)0.2793 (7)0.7384 (3)0.0524 (10)
H14A0.24760.29770.78320.063*
C15A0.17764 (17)0.0889 (7)0.7488 (3)0.0550 (9)
H15A0.18790.02380.80170.066*
C16A0.12788 (16)0.0588 (7)0.6840 (3)0.0518 (9)
H16A0.10380.07370.69200.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.047 (2)0.051 (2)0.057 (3)0.0027 (18)0.009 (2)0.004 (2)
O10.0481 (16)0.0524 (15)0.0595 (18)0.0071 (11)0.0101 (14)0.0034 (12)
O20.0481 (16)0.0583 (15)0.076 (2)0.0092 (11)0.0169 (17)0.0094 (14)
C10.057 (2)0.0479 (18)0.051 (2)0.0006 (16)0.011 (2)0.0046 (16)
C20.048 (2)0.0461 (17)0.048 (2)0.0037 (15)0.0067 (18)0.0038 (15)
C30.052 (2)0.0499 (18)0.055 (3)0.0065 (15)0.007 (2)0.0001 (17)
C40.067 (3)0.0513 (19)0.055 (3)0.0095 (18)0.005 (2)0.0019 (17)
C50.073 (3)0.0493 (19)0.060 (3)0.0042 (17)0.018 (2)0.0011 (18)
C60.063 (3)0.055 (2)0.059 (3)0.0009 (18)0.019 (2)0.0007 (19)
C110.048 (2)0.0446 (17)0.050 (2)0.0000 (14)0.0089 (19)0.0040 (15)
C120.048 (2)0.0434 (17)0.051 (2)0.0032 (14)0.0076 (18)0.0038 (16)
C130.053 (2)0.0503 (18)0.055 (2)0.0037 (15)0.0077 (19)0.0055 (17)
C140.048 (2)0.067 (2)0.055 (3)0.0032 (18)0.015 (2)0.0062 (18)
C150.068 (3)0.056 (2)0.058 (3)0.0071 (18)0.023 (2)0.0020 (19)
C160.063 (2)0.0481 (18)0.055 (2)0.0024 (17)0.013 (2)0.0005 (16)
B1A0.046 (2)0.047 (2)0.054 (3)0.0052 (17)0.014 (2)0.0037 (18)
O1A0.0457 (15)0.0466 (13)0.0511 (16)0.0035 (10)0.0094 (12)0.0007 (11)
O2A0.0480 (15)0.0478 (13)0.0608 (19)0.0040 (11)0.0061 (15)0.0059 (12)
C1A0.050 (2)0.0406 (16)0.051 (2)0.0029 (14)0.0158 (18)0.0015 (15)
C2A0.053 (2)0.0384 (16)0.053 (2)0.0001 (14)0.0180 (18)0.0041 (15)
C3A0.051 (2)0.0467 (17)0.050 (2)0.0061 (15)0.017 (2)0.0023 (15)
C4A0.065 (3)0.0436 (17)0.060 (3)0.0027 (16)0.027 (2)0.0023 (16)
C5A0.069 (3)0.0445 (17)0.055 (2)0.0043 (16)0.021 (2)0.0056 (17)
C6A0.055 (2)0.0508 (18)0.052 (2)0.0025 (16)0.0131 (19)0.0004 (17)
C11A0.037 (2)0.0417 (16)0.049 (2)0.0016 (13)0.0113 (17)0.0061 (14)
C12A0.046 (2)0.0389 (16)0.047 (2)0.0007 (13)0.0132 (17)0.0022 (14)
C13A0.052 (2)0.0458 (17)0.056 (2)0.0076 (15)0.0154 (19)0.0026 (16)
C14A0.050 (2)0.0558 (19)0.050 (2)0.0048 (15)0.0106 (19)0.0043 (16)
C15A0.063 (2)0.0461 (18)0.054 (2)0.0042 (16)0.014 (2)0.0005 (16)
C16A0.056 (2)0.0435 (17)0.057 (2)0.0063 (15)0.017 (2)0.0011 (16)
Geometric parameters (Å, º) top
B1—O21.353 (5)B1A—O2A1.359 (5)
B1—O11.387 (6)B1A—O1A1.382 (5)
B1—C11.548 (6)B1A—C1A1.543 (6)
O1—C111.391 (5)O1A—C11A1.386 (4)
O2—H20.8400O2A—H2A0.8400
C1—C61.410 (6)C1A—C6A1.403 (6)
C1—C21.416 (5)C1A—C2A1.415 (6)
C2—C31.393 (5)C2A—C3A1.392 (5)
C2—C121.465 (6)C2A—C12A1.478 (5)
C3—C41.371 (6)C3A—C4A1.395 (6)
C3—H30.9500C3A—H3A0.9500
C4—C51.405 (6)C4A—C5A1.377 (6)
C4—H40.9500C4A—H4A0.9500
C5—C61.378 (6)C5A—C6A1.380 (6)
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C11—C161.395 (6)C11A—C16A1.389 (6)
C11—C121.406 (5)C11A—C12A1.390 (5)
C12—C131.403 (5)C12A—C13A1.407 (6)
C13—C141.372 (6)C13A—C14A1.391 (6)
C13—H130.9500C13A—H13A0.9500
C14—C151.391 (6)C14A—C15A1.373 (5)
C14—H140.9500C14A—H14A0.9500
C15—C161.394 (6)C15A—C16A1.369 (6)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
O2—B1—O1118.8 (4)O2A—B1A—O1A117.5 (4)
O2—B1—C1122.7 (4)O2A—B1A—C1A123.2 (4)
O1—B1—C1118.6 (3)O1A—B1A—C1A119.3 (4)
B1—O1—C11121.5 (3)B1A—O1A—C11A121.2 (3)
B1—O2—H2109.5B1A—O2A—H2A109.5
C6—C1—C2119.8 (4)C6A—C1A—C2A119.3 (3)
C6—C1—B1122.2 (4)C6A—C1A—B1A122.4 (4)
C2—C1—B1118.0 (3)C2A—C1A—B1A118.3 (3)
C3—C2—C1118.3 (4)C3A—C2A—C1A119.1 (4)
C3—C2—C12121.7 (4)C3A—C2A—C12A122.8 (4)
C1—C2—C12119.9 (3)C1A—C2A—C12A118.0 (3)
C4—C3—C2121.4 (4)C2A—C3A—C4A120.5 (4)
C4—C3—H3119.3C2A—C3A—H3A119.7
C2—C3—H3119.3C4A—C3A—H3A119.7
C3—C4—C5120.7 (4)C5A—C4A—C3A120.2 (4)
C3—C4—H4119.7C5A—C4A—H4A119.9
C5—C4—H4119.7C3A—C4A—H4A119.9
C6—C5—C4119.3 (4)C4A—C5A—C6A120.4 (4)
C6—C5—H5120.4C4A—C5A—H5A119.8
C4—C5—H5120.4C6A—C5A—H5A119.8
C5—C6—C1120.5 (4)C5A—C6A—C1A120.5 (4)
C5—C6—H6119.7C5A—C6A—H6A119.8
C1—C6—H6119.7C1A—C6A—H6A119.8
O1—C11—C16115.5 (3)O1A—C11A—C16A115.8 (3)
O1—C11—C12122.7 (4)O1A—C11A—C12A122.2 (4)
C16—C11—C12121.8 (4)C16A—C11A—C12A122.0 (4)
C13—C12—C11116.1 (4)C11A—C12A—C13A116.2 (3)
C13—C12—C2124.6 (3)C11A—C12A—C2A121.0 (4)
C11—C12—C2119.3 (4)C13A—C12A—C2A122.8 (3)
C14—C13—C12123.1 (4)C14A—C13A—C12A122.2 (3)
C14—C13—H13118.5C14A—C13A—H13A118.9
C12—C13—H13118.5C12A—C13A—H13A118.9
C13—C14—C15119.6 (4)C15A—C14A—C13A118.8 (4)
C13—C14—H14120.2C15A—C14A—H14A120.6
C15—C14—H14120.2C13A—C14A—H14A120.6
C14—C15—C16119.6 (4)C16A—C15A—C14A121.0 (4)
C14—C15—H15120.2C16A—C15A—H15A119.5
C16—C15—H15120.2C14A—C15A—H15A119.5
C15—C16—C11119.7 (4)C15A—C16A—C11A119.6 (3)
C15—C16—H16120.1C15A—C16A—H16A120.2
C11—C16—H16120.1C11A—C16A—H16A120.2
O2—B1—O1—C11178.1 (4)O2A—B1A—O1A—C11A177.8 (3)
C1—B1—O1—C112.0 (6)C1A—B1A—O1A—C11A1.1 (5)
O2—B1—C1—C60.9 (7)O2A—B1A—C1A—C6A1.5 (6)
O1—B1—C1—C6178.9 (4)O1A—B1A—C1A—C6A179.6 (3)
O2—B1—C1—C2178.1 (4)O2A—B1A—C1A—C2A177.9 (3)
O1—B1—C1—C22.0 (6)O1A—B1A—C1A—C2A0.9 (5)
C6—C1—C2—C30.9 (6)C6A—C1A—C2A—C3A0.6 (5)
B1—C1—C2—C3180.0 (4)B1A—C1A—C2A—C3A179.9 (3)
C6—C1—C2—C12180.0 (4)C6A—C1A—C2A—C12A179.6 (3)
B1—C1—C2—C121.0 (5)B1A—C1A—C2A—C12A0.2 (5)
C1—C2—C3—C41.2 (6)C1A—C2A—C3A—C4A0.9 (5)
C12—C2—C3—C4179.7 (4)C12A—C2A—C3A—C4A179.4 (3)
C2—C3—C4—C50.9 (7)C2A—C3A—C4A—C5A0.9 (6)
C3—C4—C5—C60.4 (7)C3A—C4A—C5A—C6A0.7 (6)
C4—C5—C6—C10.1 (7)C4A—C5A—C6A—C1A0.4 (6)
C2—C1—C6—C50.4 (6)C2A—C1A—C6A—C5A0.4 (6)
B1—C1—C6—C5179.4 (4)B1A—C1A—C6A—C5A179.8 (3)
B1—O1—C11—C16179.5 (4)B1A—O1A—C11A—C16A178.9 (3)
B1—O1—C11—C120.9 (6)B1A—O1A—C11A—C12A0.5 (5)
O1—C11—C12—C13179.6 (3)O1A—C11A—C12A—C13A179.3 (3)
C16—C11—C12—C130.9 (6)C16A—C11A—C12A—C13A1.0 (5)
O1—C11—C12—C20.2 (6)O1A—C11A—C12A—C2A0.3 (5)
C16—C11—C12—C2179.3 (3)C16A—C11A—C12A—C2A178.0 (3)
C3—C2—C12—C131.3 (6)C3A—C2A—C12A—C11A179.4 (3)
C1—C2—C12—C13179.6 (3)C1A—C2A—C12A—C11A0.4 (5)
C3—C2—C12—C11178.9 (4)C3A—C2A—C12A—C13A0.3 (5)
C1—C2—C12—C110.1 (6)C1A—C2A—C12A—C13A179.4 (3)
C11—C12—C13—C142.6 (6)C11A—C12A—C13A—C14A2.0 (5)
C2—C12—C13—C14177.6 (4)C2A—C12A—C13A—C14A177.1 (3)
C12—C13—C14—C153.0 (7)C12A—C13A—C14A—C15A1.9 (6)
C13—C14—C15—C161.5 (6)C13A—C14A—C15A—C16A0.8 (6)
C14—C15—C16—C110.1 (6)C14A—C15A—C16A—C11A0.1 (6)
O1—C11—C16—C15179.2 (3)O1A—C11A—C16A—C15A178.5 (3)
C12—C11—C16—C150.4 (6)C12A—C11A—C16A—C15A0.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.842.072.884 (4)164
O2A—H2A···O1Aii0.842.062.888 (4)170
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.
(VI) 9-[(Biphenyl-2-yl)oxy]-10-oxa-9-boraphenanthrene top
Crystal data top
C24H17BO2F(000) = 2912
Mr = 348.19Dx = 1.317 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 13336 reflections
a = 20.7814 (10) Åθ = 1.9–25.8°
b = 10.3740 (4) ŵ = 0.08 mm1
c = 32.6452 (19) ÅT = 173 K
β = 93.427 (4)°Block, colourless
V = 7025.3 (6) Å30.31 × 0.22 × 0.22 mm
Z = 16
Data collection top
Stoe IPDS II two-circle
diffractometer
4375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
Graphite monochromatorθmax = 25.4°, θmin = 2.0°
ω scansh = 2425
24449 measured reflectionsk = 1212
6439 independent reflectionsl = 3739
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0858P)2]
where P = (Fo2 + 2Fc2)/3
6439 reflections(Δ/σ)max < 0.001
973 parametersΔρmax = 0.35 e Å3
650 restraintsΔρmin = 0.24 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
B10.1150 (4)0.9736 (6)0.8472 (2)0.0410 (16)
O10.1477 (2)0.9796 (4)0.81022 (13)0.0403 (10)
O20.1336 (2)0.8834 (4)0.87583 (13)0.0396 (9)
C10.0578 (3)1.0662 (6)0.85224 (19)0.0385 (14)
C20.0439 (3)1.1566 (5)0.82208 (18)0.0353 (13)
C30.0077 (3)1.2418 (6)0.8276 (2)0.0448 (16)
H30.01911.30310.80680.054*
C40.0410 (3)1.2382 (6)0.8614 (2)0.0484 (16)
H40.07471.29870.86450.058*
C50.0275 (3)1.1485 (6)0.8918 (2)0.0439 (14)
H50.05231.14380.91520.053*
C60.0248 (3)1.0635 (6)0.8869 (2)0.0491 (16)
H60.03691.00390.90800.059*
C110.1327 (3)1.0724 (6)0.78152 (19)0.0388 (14)
C120.0813 (3)1.1604 (5)0.78538 (18)0.0335 (13)
C130.0743 (3)1.2533 (5)0.7530 (2)0.0436 (15)
H130.04221.31810.75440.052*
C140.1107 (4)1.2525 (7)0.7213 (2)0.0495 (16)
H140.10321.31720.70090.059*
C150.1587 (3)1.1645 (6)0.7157 (2)0.0447 (15)
H150.18281.16500.69180.054*
C160.1705 (3)1.0721 (6)0.74782 (19)0.0415 (14)
H160.20411.01060.74610.050*
C210.1863 (3)0.8016 (5)0.87792 (19)0.0373 (13)
C220.2048 (3)0.7520 (5)0.91842 (18)0.0414 (14)
C230.2574 (3)0.6715 (6)0.9228 (2)0.0595 (18)
H230.27240.64390.94940.071*
C240.2888 (4)0.6300 (7)0.8889 (2)0.0603 (19)
H240.32270.56880.89220.072*
C250.2700 (4)0.6792 (7)0.8491 (2)0.0519 (16)
H250.29270.65500.82590.062*
C260.2191 (3)0.7613 (6)0.8450 (2)0.0421 (14)
H260.20570.79190.81850.051*
C310.1675 (3)0.7857 (6)0.95455 (19)0.0451 (15)
C320.1042 (3)0.7661 (5)0.95595 (18)0.0480 (13)
H320.08030.73690.93200.058*
C330.0722 (3)0.7877 (5)0.9919 (2)0.0569 (15)
H330.02760.76780.99240.068*
C340.1032 (4)0.8360 (6)1.0257 (2)0.0617 (19)
H340.08040.85371.04940.074*
C350.1705 (3)0.8605 (5)1.02578 (18)0.0568 (14)
H350.19330.89271.04970.068*
C360.2024 (3)0.8367 (5)0.99043 (18)0.0503 (13)
H360.24720.85410.98990.060*
B1A0.1166 (4)0.4720 (6)0.8430 (2)0.0416 (16)
O1A0.1531 (2)0.4801 (4)0.80771 (12)0.0370 (9)
O2A0.1336 (2)0.3824 (4)0.87213 (12)0.0390 (9)
C1A0.0588 (3)0.5625 (6)0.84599 (18)0.0371 (13)
C2A0.0470 (3)0.6550 (6)0.81636 (18)0.0365 (13)
C3A0.0034 (3)0.7413 (6)0.8209 (2)0.0434 (15)
H3A0.01140.80670.80080.052*
C4A0.0411 (3)0.7341 (6)0.85302 (18)0.0428 (14)
H4A0.07450.79560.85550.051*
C5A0.0319 (3)0.6380 (6)0.88267 (18)0.0406 (13)
H5A0.05990.62880.90450.049*
C6A0.0211 (3)0.5550 (6)0.87853 (18)0.0437 (15)
H6A0.03070.49200.89910.052*
C11A0.1382 (3)0.5717 (5)0.77800 (18)0.0338 (13)
C12A0.0873 (3)0.6586 (5)0.78084 (17)0.0333 (13)
C13A0.0794 (3)0.7486 (5)0.74773 (19)0.0383 (14)
H13A0.04660.81220.74820.046*
C14A0.1172 (4)0.7447 (7)0.7164 (2)0.0503 (17)
H14A0.10970.80690.69520.060*
C15A0.1657 (3)0.6586 (6)0.71212 (18)0.0416 (14)
H15A0.19070.65810.68870.050*
C16A0.1767 (3)0.5696 (6)0.74484 (19)0.0404 (14)
H16A0.21070.50850.74400.048*
C21A0.1832 (3)0.2934 (6)0.87644 (18)0.0385 (14)
C22A0.1905 (3)0.2305 (5)0.91601 (18)0.0392 (13)
C23A0.2350 (3)0.1334 (5)0.92105 (19)0.0474 (14)
H23A0.23930.08860.94650.057*
C24A0.2747 (3)0.0986 (5)0.8892 (2)0.0472 (15)
H24A0.30670.03380.89350.057*
C25A0.2663 (4)0.1611 (6)0.8511 (2)0.0558 (18)
H25A0.29200.13750.82920.067*
C26A0.2211 (3)0.2557 (6)0.8456 (2)0.0429 (15)
H26A0.21560.29680.81960.052*
C31A0.1489 (3)0.2653 (5)0.95007 (16)0.0365 (12)
C32A0.1381 (3)0.3951 (4)0.96027 (17)0.0442 (11)
H32A0.15400.46230.94390.053*
C33A0.1038 (3)0.4245 (5)0.99455 (18)0.0580 (15)
H33A0.09730.51201.00190.070*
C34A0.0792 (3)0.3267 (6)1.0179 (2)0.0571 (17)
H34A0.05590.34671.04130.069*
C35A0.0888 (4)0.2020 (7)1.0072 (2)0.0739 (18)
H35A0.07110.13521.02290.089*
C36A0.1239 (3)0.1700 (5)0.97378 (17)0.0550 (14)
H36A0.13070.08200.96720.066*
B1B0.3866 (3)0.7185 (6)0.6486 (2)0.0380 (16)
O1B0.3554 (2)0.7261 (4)0.68241 (13)0.0433 (10)
O2B0.37027 (19)0.6327 (4)0.61742 (12)0.0401 (10)
C1B0.4427 (3)0.8111 (5)0.64133 (17)0.0340 (13)
C2B0.4591 (3)0.9058 (5)0.67254 (19)0.0374 (13)
C3B0.5094 (3)0.9924 (6)0.6678 (2)0.0408 (14)
H3B0.52001.05520.68830.049*
C4B0.5447 (3)0.9854 (6)0.6317 (2)0.0463 (15)
H4B0.57991.04230.62850.056*
C5B0.5281 (3)0.8962 (6)0.6014 (2)0.0521 (16)
H5B0.55070.89600.57690.062*
C6B0.4809 (3)0.8100 (6)0.60572 (18)0.0412 (14)
H6B0.47240.74690.58500.049*
C11B0.3702 (3)0.8171 (6)0.71253 (19)0.0414 (15)
C12B0.4192 (3)0.9067 (6)0.7087 (2)0.0396 (14)
C13B0.4307 (3)0.9944 (6)0.74003 (19)0.0418 (14)
H13B0.46481.05470.73830.050*
C14B0.3923 (3)0.9974 (6)0.7754 (2)0.0435 (15)
H14B0.40011.05720.79720.052*
C15B0.3425 (3)0.9054 (6)0.77539 (19)0.0444 (14)
H15B0.31480.90630.79750.053*
C16B0.3322 (3)0.8170 (6)0.7460 (2)0.0476 (16)
H16B0.29910.75460.74800.057*
C21B0.3184 (3)0.5465 (6)0.61356 (19)0.0377 (13)
C22B0.3002 (3)0.5078 (5)0.5757 (2)0.0437 (15)
C23B0.2458 (3)0.4235 (5)0.57083 (19)0.0479 (14)
H23B0.23200.39380.54420.057*
C24B0.2134 (3)0.3848 (6)0.6040 (2)0.0569 (18)
H24B0.17630.33170.60030.068*
C25B0.2340 (3)0.4220 (6)0.6415 (2)0.0466 (16)
H25B0.21260.39050.66440.056*
C26B0.2872 (3)0.5074 (6)0.6484 (2)0.0455 (16)
H26B0.30070.53640.67510.055*
C31B0.3342 (3)0.5423 (4)0.53833 (16)0.0370 (12)
C32B0.4001 (3)0.5170 (5)0.53635 (18)0.0473 (12)
H32B0.42360.48330.55980.057*
C33B0.4314 (3)0.5398 (5)0.5011 (2)0.0539 (14)
H33B0.47620.52210.50060.065*
C34B0.3981 (3)0.5887 (5)0.46619 (19)0.0507 (15)
H34B0.41970.60450.44180.061*
C35B0.3339 (3)0.6132 (5)0.46773 (18)0.0581 (15)
H35B0.31110.64790.44410.070*
C36B0.3007 (3)0.5894 (5)0.50244 (17)0.0502 (13)
H36B0.25560.60470.50220.060*
B1C0.3851 (3)0.2221 (6)0.65528 (19)0.0296 (13)
O1C0.3515 (2)0.2320 (4)0.68891 (13)0.0406 (10)
O2C0.36904 (19)0.1389 (4)0.62396 (12)0.0392 (9)
C1C0.4420 (3)0.3140 (5)0.64907 (18)0.0353 (13)
C2C0.4559 (3)0.4101 (5)0.68031 (17)0.0337 (13)
C3C0.5068 (3)0.4990 (6)0.67550 (19)0.0375 (13)
H3C0.51480.56560.69510.045*
C4C0.5452 (3)0.4885 (7)0.6417 (2)0.0486 (16)
H4C0.58000.54640.63870.058*
C5C0.5321 (3)0.3943 (7)0.6133 (2)0.0521 (17)
H5C0.55820.38970.59040.063*
C6C0.4838 (3)0.3062 (6)0.61578 (19)0.0414 (14)
H6C0.47790.24050.59570.050*
C11C0.3663 (3)0.3208 (6)0.71934 (18)0.0368 (13)
C12C0.4153 (3)0.4135 (6)0.71620 (18)0.0367 (13)
C13C0.4263 (3)0.4988 (6)0.7474 (2)0.0422 (14)
H13C0.46050.55900.74580.051*
C14C0.3886 (3)0.5011 (5)0.78222 (18)0.0356 (13)
H14C0.39630.56130.80390.043*
C15C0.3389 (3)0.4085 (6)0.7827 (2)0.0482 (16)
H15C0.31150.40850.80500.058*
C16C0.3286 (3)0.3205 (6)0.75290 (19)0.0442 (15)
H16C0.29550.25800.75480.053*
C21C0.3208 (3)0.0459 (6)0.6190 (2)0.0400 (14)
C22C0.3140 (3)0.0108 (5)0.58218 (18)0.0383 (13)
C23C0.2655 (3)0.1077 (6)0.5770 (2)0.0542 (17)
H23C0.25960.15060.55140.065*
C24C0.2271 (4)0.1406 (7)0.6081 (3)0.0620 (19)
H24C0.19490.20500.60380.074*
C25C0.2351 (3)0.0824 (6)0.6439 (2)0.0498 (16)
H25C0.20810.10550.66520.060*
C26C0.2832 (3)0.0141 (6)0.6516 (2)0.0446 (15)
H26C0.28930.05470.67760.054*
C31C0.3514 (3)0.0237 (6)0.54633 (19)0.0470 (16)
C32C0.3646 (3)0.1473 (5)0.53533 (17)0.0459 (12)
H32C0.34990.21630.55150.055*
C33C0.3990 (3)0.1752 (5)0.50110 (17)0.0545 (14)
H33C0.40730.26210.49400.065*
C34C0.4208 (4)0.0764 (8)0.4776 (2)0.075 (2)
H34C0.44220.09510.45340.089*
C35C0.4117 (3)0.0487 (6)0.48888 (19)0.0638 (16)
H35C0.42910.11620.47330.077*
C36C0.3776 (3)0.0784 (5)0.52258 (18)0.0563 (14)
H36C0.37150.16580.53010.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.055 (4)0.034 (3)0.034 (3)0.005 (3)0.004 (3)0.005 (2)
O10.040 (2)0.0369 (19)0.044 (2)0.0067 (18)0.0008 (18)0.0043 (17)
O20.037 (2)0.0320 (18)0.049 (2)0.0041 (17)0.0071 (17)0.0039 (17)
C10.029 (3)0.035 (3)0.051 (3)0.001 (2)0.005 (3)0.007 (2)
C20.028 (3)0.032 (3)0.045 (3)0.005 (2)0.003 (2)0.007 (2)
C30.038 (3)0.032 (3)0.063 (4)0.004 (2)0.012 (3)0.001 (3)
C40.043 (3)0.028 (3)0.074 (4)0.008 (2)0.003 (3)0.001 (3)
C50.043 (3)0.040 (3)0.050 (3)0.006 (2)0.009 (3)0.005 (2)
C60.049 (4)0.038 (3)0.058 (4)0.007 (3)0.014 (3)0.005 (3)
C110.032 (3)0.037 (3)0.047 (3)0.002 (2)0.007 (2)0.002 (2)
C120.025 (3)0.026 (2)0.048 (3)0.002 (2)0.008 (2)0.003 (2)
C130.044 (3)0.026 (3)0.058 (4)0.003 (2)0.016 (3)0.007 (2)
C140.047 (4)0.050 (3)0.051 (4)0.003 (3)0.005 (3)0.016 (3)
C150.040 (3)0.046 (3)0.047 (3)0.008 (3)0.006 (3)0.010 (2)
C160.039 (3)0.035 (3)0.050 (3)0.007 (2)0.004 (3)0.003 (2)
C210.039 (3)0.024 (2)0.047 (3)0.002 (2)0.008 (3)0.007 (2)
C220.034 (3)0.039 (3)0.049 (3)0.002 (2)0.008 (2)0.011 (2)
C230.055 (4)0.056 (4)0.067 (4)0.026 (3)0.003 (3)0.015 (3)
C240.059 (4)0.058 (4)0.064 (4)0.029 (3)0.011 (3)0.011 (3)
C250.056 (4)0.044 (3)0.055 (4)0.010 (3)0.000 (3)0.002 (3)
C260.042 (3)0.037 (3)0.048 (4)0.003 (3)0.002 (3)0.002 (3)
C310.045 (4)0.039 (3)0.051 (3)0.013 (2)0.001 (3)0.010 (2)
C320.046 (3)0.042 (3)0.056 (3)0.001 (2)0.006 (3)0.005 (2)
C330.051 (3)0.046 (3)0.075 (4)0.004 (3)0.010 (3)0.005 (3)
C340.093 (6)0.036 (3)0.058 (4)0.005 (3)0.019 (4)0.005 (3)
C350.072 (4)0.041 (3)0.054 (3)0.002 (3)0.014 (3)0.008 (2)
C360.052 (3)0.043 (3)0.054 (3)0.002 (2)0.010 (2)0.008 (2)
B1A0.053 (4)0.034 (3)0.037 (3)0.014 (3)0.000 (3)0.003 (3)
O1A0.041 (2)0.0325 (18)0.038 (2)0.0022 (17)0.0059 (17)0.0066 (16)
O2A0.039 (2)0.0331 (18)0.045 (2)0.0009 (17)0.0010 (17)0.0031 (16)
C1A0.034 (3)0.038 (3)0.038 (3)0.006 (2)0.007 (2)0.003 (2)
C2A0.033 (3)0.034 (3)0.042 (3)0.005 (2)0.000 (2)0.004 (2)
C3A0.049 (4)0.030 (3)0.049 (3)0.007 (2)0.015 (3)0.000 (2)
C4A0.047 (3)0.041 (3)0.040 (3)0.010 (2)0.006 (3)0.001 (2)
C5A0.031 (3)0.048 (3)0.043 (3)0.001 (2)0.001 (2)0.000 (2)
C6A0.049 (4)0.044 (3)0.037 (3)0.001 (3)0.007 (3)0.001 (2)
C11A0.031 (3)0.030 (3)0.040 (3)0.003 (2)0.002 (2)0.002 (2)
C12A0.036 (3)0.023 (2)0.040 (3)0.002 (2)0.010 (2)0.003 (2)
C13A0.036 (3)0.029 (3)0.048 (3)0.000 (2)0.009 (3)0.010 (2)
C14A0.051 (4)0.051 (4)0.048 (3)0.010 (3)0.002 (3)0.018 (3)
C15A0.046 (3)0.043 (3)0.036 (3)0.006 (3)0.005 (2)0.010 (2)
C16A0.044 (3)0.030 (3)0.047 (3)0.002 (2)0.002 (3)0.003 (2)
C21A0.040 (3)0.034 (3)0.041 (3)0.005 (3)0.007 (2)0.011 (2)
C22A0.047 (3)0.025 (2)0.045 (3)0.001 (2)0.001 (2)0.009 (2)
C23A0.047 (3)0.033 (3)0.061 (3)0.003 (2)0.006 (3)0.009 (2)
C24A0.041 (3)0.032 (3)0.068 (4)0.003 (2)0.002 (3)0.000 (2)
C25A0.062 (4)0.043 (3)0.061 (4)0.008 (3)0.004 (3)0.008 (3)
C26A0.041 (3)0.038 (3)0.050 (4)0.003 (3)0.007 (3)0.004 (3)
C31A0.040 (3)0.028 (2)0.041 (3)0.007 (2)0.004 (2)0.0025 (19)
C32A0.046 (3)0.042 (3)0.045 (3)0.003 (2)0.002 (2)0.001 (2)
C33A0.067 (4)0.053 (3)0.054 (3)0.005 (3)0.005 (3)0.008 (3)
C34A0.070 (5)0.058 (3)0.043 (3)0.008 (3)0.001 (3)0.001 (3)
C35A0.102 (5)0.069 (4)0.051 (4)0.014 (4)0.012 (3)0.006 (3)
C36A0.081 (4)0.042 (3)0.041 (3)0.002 (3)0.001 (3)0.010 (2)
B1B0.024 (3)0.033 (3)0.055 (4)0.007 (3)0.013 (3)0.000 (3)
O1B0.046 (2)0.035 (2)0.048 (2)0.0097 (18)0.006 (2)0.0032 (18)
O2B0.038 (2)0.0381 (19)0.044 (2)0.0135 (18)0.0038 (17)0.0079 (17)
C1B0.036 (3)0.028 (2)0.037 (3)0.003 (2)0.007 (2)0.002 (2)
C2B0.036 (3)0.028 (3)0.046 (3)0.000 (2)0.016 (2)0.003 (2)
C3B0.034 (3)0.034 (3)0.054 (4)0.005 (2)0.001 (3)0.000 (3)
C4B0.031 (3)0.047 (3)0.060 (4)0.003 (3)0.001 (3)0.011 (3)
C5B0.051 (4)0.052 (3)0.052 (4)0.003 (3)0.001 (3)0.002 (3)
C6B0.041 (3)0.039 (3)0.044 (3)0.003 (2)0.007 (2)0.006 (2)
C11B0.049 (4)0.029 (3)0.045 (3)0.002 (3)0.008 (3)0.003 (2)
C12B0.038 (3)0.034 (3)0.046 (3)0.003 (2)0.007 (3)0.003 (2)
C13B0.031 (3)0.043 (3)0.051 (3)0.006 (2)0.002 (3)0.004 (3)
C14B0.043 (3)0.032 (3)0.054 (4)0.003 (2)0.007 (3)0.000 (2)
C15B0.047 (3)0.042 (3)0.044 (3)0.001 (3)0.004 (3)0.000 (2)
C16B0.040 (4)0.044 (3)0.058 (4)0.002 (3)0.004 (3)0.001 (3)
C21B0.025 (3)0.034 (3)0.055 (3)0.001 (2)0.004 (2)0.002 (2)
C22B0.045 (3)0.030 (3)0.057 (3)0.005 (2)0.008 (3)0.008 (2)
C23B0.034 (3)0.049 (3)0.061 (3)0.006 (2)0.002 (3)0.022 (3)
C24B0.035 (3)0.050 (3)0.085 (5)0.012 (3)0.004 (3)0.017 (3)
C25B0.035 (3)0.041 (3)0.066 (4)0.009 (2)0.020 (3)0.010 (3)
C26B0.046 (4)0.033 (3)0.057 (4)0.009 (3)0.003 (3)0.004 (3)
C31B0.038 (3)0.024 (2)0.048 (3)0.005 (2)0.006 (2)0.0087 (19)
C32B0.040 (3)0.043 (3)0.058 (3)0.001 (2)0.004 (3)0.007 (2)
C33B0.042 (3)0.048 (3)0.071 (4)0.002 (2)0.004 (3)0.001 (3)
C34B0.057 (4)0.042 (3)0.054 (4)0.002 (3)0.005 (3)0.000 (2)
C35B0.074 (4)0.050 (3)0.048 (3)0.003 (3)0.012 (3)0.006 (2)
C36B0.045 (3)0.051 (3)0.053 (3)0.006 (2)0.011 (2)0.016 (2)
B1C0.023 (3)0.031 (3)0.035 (3)0.005 (2)0.003 (2)0.003 (2)
O1C0.042 (2)0.0347 (19)0.044 (2)0.0072 (18)0.0048 (18)0.0008 (17)
O2C0.036 (2)0.039 (2)0.043 (2)0.0076 (17)0.0035 (17)0.0074 (17)
C1C0.036 (3)0.029 (2)0.042 (3)0.003 (2)0.002 (2)0.003 (2)
C2C0.034 (3)0.031 (3)0.036 (3)0.001 (2)0.006 (2)0.003 (2)
C3C0.034 (3)0.038 (3)0.040 (3)0.003 (2)0.002 (2)0.000 (2)
C4C0.035 (3)0.058 (4)0.053 (4)0.001 (3)0.005 (3)0.013 (3)
C5C0.043 (3)0.070 (4)0.045 (3)0.001 (3)0.014 (3)0.013 (3)
C6C0.036 (3)0.044 (3)0.044 (3)0.005 (3)0.008 (2)0.002 (2)
C11C0.043 (3)0.031 (3)0.037 (3)0.002 (2)0.001 (3)0.002 (2)
C12C0.029 (3)0.040 (3)0.041 (3)0.008 (2)0.006 (2)0.007 (2)
C13C0.034 (3)0.041 (3)0.051 (4)0.000 (2)0.005 (3)0.003 (3)
C14C0.038 (3)0.029 (2)0.039 (3)0.001 (2)0.001 (2)0.006 (2)
C15C0.038 (3)0.041 (3)0.067 (4)0.001 (3)0.010 (3)0.001 (3)
C16C0.039 (3)0.049 (3)0.045 (3)0.001 (3)0.008 (3)0.004 (3)
C21C0.028 (3)0.032 (3)0.059 (4)0.003 (2)0.002 (3)0.009 (3)
C22C0.031 (3)0.035 (3)0.047 (3)0.008 (2)0.008 (2)0.000 (2)
C23C0.066 (4)0.042 (3)0.053 (3)0.014 (3)0.008 (3)0.003 (3)
C24C0.056 (4)0.051 (3)0.077 (5)0.027 (3)0.008 (3)0.005 (3)
C25C0.041 (4)0.039 (3)0.071 (4)0.009 (3)0.020 (3)0.003 (3)
C26C0.047 (4)0.039 (3)0.048 (4)0.004 (3)0.001 (3)0.001 (3)
C31C0.055 (4)0.042 (3)0.043 (3)0.011 (3)0.003 (3)0.009 (2)
C32C0.047 (3)0.039 (2)0.051 (3)0.006 (2)0.003 (2)0.008 (2)
C33C0.063 (4)0.055 (3)0.046 (3)0.013 (3)0.002 (3)0.004 (2)
C34C0.099 (6)0.064 (4)0.064 (4)0.015 (4)0.033 (4)0.011 (4)
C35C0.084 (5)0.054 (3)0.053 (3)0.008 (3)0.011 (3)0.006 (3)
C36C0.078 (4)0.044 (3)0.047 (3)0.006 (3)0.005 (3)0.005 (2)
Geometric parameters (Å, º) top
B1—O21.363 (8)B1B—O1B1.317 (8)
B1—O11.420 (8)B1B—O2B1.378 (8)
B1—C11.546 (10)B1B—C1B1.539 (9)
O1—C111.366 (7)O1B—C11B1.384 (7)
O2—C211.384 (7)O2B—C21B1.400 (7)
C1—C61.357 (9)C1B—C2B1.441 (8)
C1—C21.378 (9)C1B—C6B1.447 (8)
C2—C31.409 (9)C2B—C3B1.394 (9)
C2—C121.466 (8)C2B—C12B1.484 (9)
C3—C41.338 (10)C3B—C4B1.427 (9)
C3—H30.9500C3B—H3B0.9500
C4—C51.377 (9)C4B—C5B1.385 (9)
C4—H40.9500C4B—H4B0.9500
C5—C61.416 (9)C5B—C6B1.341 (9)
C5—H50.9500C5B—H5B0.9500
C6—H60.9500C6B—H6B0.9500
C11—C161.389 (9)C11B—C16B1.385 (9)
C11—C121.417 (8)C11B—C12B1.390 (9)
C12—C131.432 (8)C12B—C13B1.378 (9)
C13—C141.318 (9)C13B—C14B1.442 (9)
C13—H130.9500C13B—H13B0.9500
C14—C151.373 (10)C14B—C15B1.407 (9)
C14—H140.9500C14B—H14B0.9500
C15—C161.432 (8)C15B—C16B1.336 (9)
C15—H150.9500C15B—H15B0.9500
C16—H160.9500C16B—H16B0.9500
C21—C261.371 (9)C21B—C22B1.334 (9)
C21—C221.449 (8)C21B—C26B1.402 (9)
C22—C231.377 (8)C22B—C23B1.430 (8)
C22—C311.491 (9)C22B—C31B1.489 (8)
C23—C241.384 (10)C23B—C24B1.370 (9)
C23—H230.9500C23B—H23B0.9500
C24—C251.429 (10)C24B—C25B1.329 (10)
C24—H240.9500C24B—H24B0.9500
C25—C261.359 (10)C25B—C26B1.423 (9)
C25—H250.9500C25B—H25B0.9500
C26—H260.9500C26B—H26B0.9500
C31—C321.334 (8)C31B—C32B1.398 (7)
C31—C361.441 (8)C31B—C36B1.414 (7)
C32—C331.402 (8)C32B—C33B1.375 (8)
C32—H320.9500C32B—H32B0.9500
C33—C341.340 (10)C33B—C34B1.395 (8)
C33—H330.9500C33B—H33B0.9500
C34—C351.422 (9)C34B—C35B1.361 (9)
C34—H340.9500C34B—H34B0.9500
C35—C361.387 (8)C35B—C36B1.384 (8)
C35—H350.9500C35B—H35B0.9500
C36—H360.9500C36B—H36B0.9500
B1A—O2A1.361 (8)B1C—O1C1.341 (7)
B1A—O1A1.420 (8)B1C—O2C1.364 (7)
B1A—C1A1.532 (10)B1C—C1C1.541 (8)
O1A—C11A1.380 (7)O1C—C11C1.376 (7)
O2A—C21A1.383 (7)O2C—C21C1.394 (7)
C1A—C6A1.360 (8)C1C—C6C1.433 (8)
C1A—C2A1.375 (9)C1C—C2C1.443 (8)
C2A—C3A1.392 (9)C2C—C3C1.419 (8)
C2A—C12A1.470 (8)C2C—C12C1.485 (8)
C3A—C4A1.349 (9)C3C—C4C1.404 (9)
C3A—H3A0.9500C3C—H3C0.9500
C4A—C5A1.395 (8)C4C—C5C1.364 (10)
C4A—H4A0.9500C4C—H4C0.9500
C5A—C6A1.412 (9)C5C—C6C1.363 (9)
C5A—H5A0.9500C5C—H5C0.9500
C6A—H6A0.9500C6C—H6C0.9500
C11A—C16A1.385 (8)C11C—C16C1.384 (9)
C11A—C12A1.398 (8)C11C—C12C1.408 (9)
C12A—C13A1.430 (8)C12C—C13C1.359 (9)
C13A—C14A1.328 (9)C13C—C14C1.420 (9)
C13A—H13A0.9500C13C—H13C0.9500
C14A—C15A1.360 (10)C14C—C15C1.412 (9)
C14A—H14A0.9500C14C—H14C0.9500
C15A—C16A1.420 (8)C15C—C16C1.341 (9)
C15A—H15A0.9500C15C—H15C0.9500
C16A—H16A0.9500C16C—H16C0.9500
C21A—C26A1.372 (9)C21C—C22C1.339 (9)
C21A—C22A1.447 (8)C21C—C26C1.397 (9)
C22A—C23A1.371 (8)C22C—C23C1.428 (8)
C22A—C31A1.493 (8)C22C—C31C1.486 (8)
C23A—C24A1.412 (9)C23C—C24C1.369 (10)
C23A—H23A0.9500C23C—H23C0.9500
C24A—C25A1.404 (10)C24C—C25C1.319 (11)
C24A—H24A0.9500C24C—H24C0.9500
C25A—C26A1.363 (10)C25C—C26C1.426 (9)
C25A—H25A0.9500C25C—H25C0.9500
C26A—H26A0.9500C26C—H26C0.9500
C31A—C36A1.377 (7)C31C—C32C1.364 (8)
C31A—C32A1.408 (7)C31C—C36C1.439 (8)
C32A—C33A1.395 (7)C32C—C33C1.393 (7)
C32A—H32A0.9500C32C—H32C0.9500
C33A—C34A1.386 (8)C33C—C34C1.373 (9)
C33A—H33A0.9500C33C—H33C0.9500
C34A—C35A1.358 (9)C34C—C35C1.364 (10)
C34A—H34A0.9500C34C—H34C0.9500
C35A—C36A1.388 (8)C35C—C36C1.378 (8)
C35A—H35A0.9500C35C—H35C0.9500
C36A—H36A0.9500C36C—H36C0.9500
O2—B1—O1118.9 (6)O1B—B1B—O2B123.1 (5)
O2—B1—C1122.8 (6)O1B—B1B—C1B120.4 (5)
O1—B1—C1118.3 (6)O2B—B1B—C1B116.5 (6)
C11—O1—B1120.8 (5)B1B—O1B—C11B122.5 (5)
B1—O2—C21130.2 (5)B1B—O2B—C21B129.3 (5)
C6—C1—C2121.0 (6)C2B—C1B—C6B117.1 (5)
C6—C1—B1120.5 (6)C2B—C1B—B1B117.8 (5)
C2—C1—B1118.4 (6)C6B—C1B—B1B125.1 (5)
C1—C2—C3117.7 (6)C3B—C2B—C1B120.6 (6)
C1—C2—C12120.2 (5)C3B—C2B—C12B122.8 (5)
C3—C2—C12122.1 (5)C1B—C2B—C12B116.6 (5)
C4—C3—C2121.5 (6)C2B—C3B—C4B119.0 (6)
C4—C3—H3119.2C2B—C3B—H3B120.5
C2—C3—H3119.2C4B—C3B—H3B120.5
C3—C4—C5121.3 (6)C5B—C4B—C3B120.4 (6)
C3—C4—H4119.4C5B—C4B—H4B119.8
C5—C4—H4119.4C3B—C4B—H4B119.8
C4—C5—C6117.7 (6)C6B—C5B—C4B121.5 (6)
C4—C5—H5121.2C6B—C5B—H5B119.3
C6—C5—H5121.2C4B—C5B—H5B119.3
C1—C6—C5120.7 (6)C5B—C6B—C1B121.4 (6)
C1—C6—H6119.6C5B—C6B—H6B119.3
C5—C6—H6119.6C1B—C6B—H6B119.3
O1—C11—C16115.2 (5)O1B—C11B—C16B116.6 (6)
O1—C11—C12122.3 (5)O1B—C11B—C12B121.7 (6)
C16—C11—C12122.5 (6)C16B—C11B—C12B121.7 (6)
C11—C12—C13114.3 (6)C13B—C12B—C11B118.1 (6)
C11—C12—C2119.7 (5)C13B—C12B—C2B120.9 (6)
C13—C12—C2125.9 (5)C11B—C12B—C2B120.9 (6)
C14—C13—C12122.5 (6)C12B—C13B—C14B121.8 (6)
C14—C13—H13118.7C12B—C13B—H13B119.1
C12—C13—H13118.7C14B—C13B—H13B119.1
C13—C14—C15124.4 (6)C15B—C14B—C13B115.3 (6)
C13—C14—H14117.8C15B—C14B—H14B122.3
C15—C14—H14117.8C13B—C14B—H14B122.3
C14—C15—C16116.2 (6)C16B—C15B—C14B123.5 (6)
C14—C15—H15121.9C16B—C15B—H15B118.3
C16—C15—H15121.9C14B—C15B—H15B118.3
C11—C16—C15119.9 (6)C15B—C16B—C11B119.5 (6)
C11—C16—H16120.0C15B—C16B—H16B120.3
C15—C16—H16120.0C11B—C16B—H16B120.3
C26—C21—O2125.3 (5)C22B—C21B—O2B116.8 (5)
C26—C21—C22119.3 (5)C22B—C21B—C26B123.0 (6)
O2—C21—C22115.4 (5)O2B—C21B—C26B120.2 (5)
C23—C22—C21118.4 (6)C21B—C22B—C23B117.7 (6)
C23—C22—C31120.5 (5)C21B—C22B—C31B124.3 (5)
C21—C22—C31121.1 (5)C23B—C22B—C31B117.9 (5)
C22—C23—C24121.0 (6)C24B—C23B—C22B121.0 (6)
C22—C23—H23119.5C24B—C23B—H23B119.5
C24—C23—H23119.5C22B—C23B—H23B119.5
C23—C24—C25119.9 (6)C25B—C24B—C23B119.7 (6)
C23—C24—H24120.0C25B—C24B—H24B120.1
C25—C24—H24120.0C23B—C24B—H24B120.1
C26—C25—C24118.8 (7)C24B—C25B—C26B122.1 (6)
C26—C25—H25120.6C24B—C25B—H25B119.0
C24—C25—H25120.6C26B—C25B—H25B119.0
C25—C26—C21122.4 (6)C21B—C26B—C25B116.4 (6)
C25—C26—H26118.8C21B—C26B—H26B121.8
C21—C26—H26118.8C25B—C26B—H26B121.8
C32—C31—C36118.5 (6)C32B—C31B—C36B117.5 (5)
C32—C31—C22123.5 (6)C32B—C31B—C22B120.4 (5)
C36—C31—C22118.0 (5)C36B—C31B—C22B121.8 (5)
C31—C32—C33121.5 (6)C33B—C32B—C31B121.4 (5)
C31—C32—H32119.2C33B—C32B—H32B119.3
C33—C32—H32119.2C31B—C32B—H32B119.3
C34—C33—C32121.3 (6)C32B—C33B—C34B120.6 (6)
C34—C33—H33119.3C32B—C33B—H33B119.7
C32—C33—H33119.3C34B—C33B—H33B119.7
C33—C34—C35119.6 (6)C35B—C34B—C33B118.5 (6)
C33—C34—H34120.2C35B—C34B—H34B120.7
C35—C34—H34120.2C33B—C34B—H34B120.7
C36—C35—C34119.0 (6)C34B—C35B—C36B122.3 (6)
C36—C35—H35120.5C34B—C35B—H35B118.8
C34—C35—H35120.5C36B—C35B—H35B118.8
C35—C36—C31120.0 (5)C35B—C36B—C31B119.7 (5)
C35—C36—H36120.0C35B—C36B—H36B120.2
C31—C36—H36120.0C31B—C36B—H36B120.2
O2A—B1A—O1A118.5 (6)O1C—B1C—O2C123.0 (5)
O2A—B1A—C1A123.1 (6)O1C—B1C—C1C120.2 (5)
O1A—B1A—C1A118.3 (5)O2C—B1C—C1C116.6 (5)
C11A—O1A—B1A120.2 (5)B1C—O1C—C11C122.5 (5)
B1A—O2A—C21A133.4 (5)B1C—O2C—C21C131.8 (5)
C6A—C1A—C2A120.2 (6)C6C—C1C—C2C118.1 (5)
C6A—C1A—B1A120.3 (6)C6C—C1C—B1C124.7 (5)
C2A—C1A—B1A119.4 (5)C2C—C1C—B1C117.1 (5)
C1A—C2A—C3A118.6 (6)C3C—C2C—C1C119.3 (5)
C1A—C2A—C12A119.1 (5)C3C—C2C—C12C122.3 (5)
C3A—C2A—C12A122.3 (5)C1C—C2C—C12C118.4 (5)
C4A—C3A—C2A121.5 (6)C4C—C3C—C2C120.0 (6)
C4A—C3A—H3A119.3C4C—C3C—H3C120.0
C2A—C3A—H3A119.3C2C—C3C—H3C120.0
C3A—C4A—C5A121.2 (6)C5C—C4C—C3C119.4 (6)
C3A—C4A—H4A119.4C5C—C4C—H4C120.3
C5A—C4A—H4A119.4C3C—C4C—H4C120.3
C4A—C5A—C6A116.4 (6)C6C—C5C—C4C123.9 (6)
C4A—C5A—H5A121.8C6C—C5C—H5C118.1
C6A—C5A—H5A121.8C4C—C5C—H5C118.1
C1A—C6A—C5A122.0 (6)C5C—C6C—C1C119.3 (6)
C1A—C6A—H6A119.0C5C—C6C—H6C120.3
C5A—C6A—H6A119.0C1C—C6C—H6C120.3
O1A—C11A—C16A115.0 (5)O1C—C11C—C16C117.2 (6)
O1A—C11A—C12A122.5 (5)O1C—C11C—C12C122.4 (5)
C16A—C11A—C12A122.5 (5)C16C—C11C—C12C120.3 (6)
C11A—C12A—C13A115.1 (5)C13C—C12C—C11C118.8 (5)
C11A—C12A—C2A120.3 (5)C13C—C12C—C2C121.9 (6)
C13A—C12A—C2A124.6 (5)C11C—C12C—C2C119.2 (5)
C14A—C13A—C12A121.1 (6)C12C—C13C—C14C122.3 (6)
C14A—C13A—H13A119.4C12C—C13C—H13C118.9
C12A—C13A—H13A119.4C14C—C13C—H13C118.9
C13A—C14A—C15A125.1 (6)C15C—C14C—C13C115.9 (6)
C13A—C14A—H14A117.5C15C—C14C—H14C122.0
C15A—C14A—H14A117.5C13C—C14C—H14C122.0
C14A—C15A—C16A116.0 (6)C16C—C15C—C14C122.7 (6)
C14A—C15A—H15A122.0C16C—C15C—H15C118.7
C16A—C15A—H15A122.0C14C—C15C—H15C118.7
C11A—C16A—C15A120.2 (6)C15C—C16C—C11C120.0 (6)
C11A—C16A—H16A119.9C15C—C16C—H16C120.0
C15A—C16A—H16A119.9C11C—C16C—H16C120.0
C26A—C21A—O2A124.9 (5)C22C—C21C—O2C116.3 (5)
C26A—C21A—C22A119.5 (5)C22C—C21C—C26C123.2 (6)
O2A—C21A—C22A115.4 (5)O2C—C21C—C26C120.5 (6)
C23A—C22A—C21A118.2 (6)C21C—C22C—C23C116.8 (6)
C23A—C22A—C31A120.3 (5)C21C—C22C—C31C124.8 (5)
C21A—C22A—C31A121.4 (5)C23C—C22C—C31C118.4 (5)
C22A—C23A—C24A121.2 (6)C24C—C23C—C22C121.8 (6)
C22A—C23A—H23A119.4C24C—C23C—H23C119.1
C24A—C23A—H23A119.4C22C—C23C—H23C119.1
C25A—C24A—C23A119.2 (6)C25C—C24C—C23C119.7 (6)
C25A—C24A—H24A120.4C25C—C24C—H24C120.2
C23A—C24A—H24A120.4C23C—C24C—H24C120.2
C26A—C25A—C24A119.8 (7)C24C—C25C—C26C121.8 (6)
C26A—C25A—H25A120.1C24C—C25C—H25C119.1
C24A—C25A—H25A120.1C26C—C25C—H25C119.1
C25A—C26A—C21A122.1 (6)C21C—C26C—C25C116.7 (6)
C25A—C26A—H26A119.0C21C—C26C—H26C121.6
C21A—C26A—H26A119.0C25C—C26C—H26C121.6
C36A—C31A—C32A118.9 (5)C32C—C31C—C36C117.5 (5)
C36A—C31A—C22A120.0 (4)C32C—C31C—C22C123.8 (5)
C32A—C31A—C22A121.0 (4)C36C—C31C—C22C118.7 (5)
C33A—C32A—C31A119.7 (5)C31C—C32C—C33C121.8 (5)
C33A—C32A—H32A120.2C31C—C32C—H32C119.1
C31A—C32A—H32A120.2C33C—C32C—H32C119.1
C34A—C33A—C32A120.3 (5)C34C—C33C—C32C119.7 (5)
C34A—C33A—H33A119.9C34C—C33C—H33C120.1
C32A—C33A—H33A119.9C32C—C33C—H33C120.1
C35A—C34A—C33A119.4 (6)C35C—C34C—C33C120.2 (7)
C35A—C34A—H34A120.3C35C—C34C—H34C119.9
C33A—C34A—H34A120.3C33C—C34C—H34C119.9
C34A—C35A—C36A121.6 (6)C34C—C35C—C36C120.9 (6)
C34A—C35A—H35A119.2C34C—C35C—H35C119.6
C36A—C35A—H35A119.2C36C—C35C—H35C119.6
C31A—C36A—C35A120.2 (5)C35C—C36C—C31C119.7 (5)
C31A—C36A—H36A119.9C35C—C36C—H36C120.2
C35A—C36A—H36A119.9C31C—C36C—H36C120.2
O2—B1—O1—C11176.9 (5)O2B—B1B—O1B—C11B176.6 (5)
C1—B1—O1—C115.8 (8)C1B—B1B—O1B—C11B1.1 (9)
O1—B1—O2—C219.1 (9)O1B—B1B—O2B—C21B4.3 (10)
C1—B1—O2—C21173.7 (5)C1B—B1B—O2B—C21B173.4 (5)
O2—B1—C1—C62.3 (9)O1B—B1B—C1B—C2B0.5 (8)
O1—B1—C1—C6179.5 (5)O2B—B1B—C1B—C2B177.4 (5)
O2—B1—C1—C2178.2 (5)O1B—B1B—C1B—C6B178.8 (5)
O1—B1—C1—C24.5 (8)O2B—B1B—C1B—C6B3.3 (9)
C6—C1—C2—C33.0 (8)C6B—C1B—C2B—C3B0.6 (8)
B1—C1—C2—C3178.9 (5)B1B—C1B—C2B—C3B180.0 (5)
C6—C1—C2—C12178.3 (5)C6B—C1B—C2B—C12B179.5 (5)
B1—C1—C2—C122.4 (8)B1B—C1B—C2B—C12B1.2 (8)
C1—C2—C3—C42.0 (9)C1B—C2B—C3B—C4B0.5 (9)
C12—C2—C3—C4179.4 (6)C12B—C2B—C3B—C4B179.2 (5)
C2—C3—C4—C51.9 (10)C2B—C3B—C4B—C5B1.8 (9)
C3—C4—C5—C62.6 (10)C3B—C4B—C5B—C6B3.4 (10)
C2—C1—C6—C53.9 (9)C4B—C5B—C6B—C1B3.6 (10)
B1—C1—C6—C5179.7 (6)C2B—C1B—C6B—C5B2.2 (8)
C4—C5—C6—C13.6 (9)B1B—C1B—C6B—C5B178.5 (6)
B1—O1—C11—C16176.7 (5)B1B—O1B—C11B—C16B177.9 (6)
B1—O1—C11—C125.0 (8)B1B—O1B—C11B—C12B0.1 (9)
O1—C11—C12—C13178.0 (5)O1B—C11B—C12B—C13B179.8 (5)
C16—C11—C12—C133.7 (8)C16B—C11B—C12B—C13B2.0 (9)
O1—C11—C12—C22.6 (8)O1B—C11B—C12B—C2B1.8 (9)
C16—C11—C12—C2179.1 (5)C16B—C11B—C12B—C2B179.6 (6)
C1—C2—C12—C111.4 (8)C3B—C2B—C12B—C13B0.5 (9)
C3—C2—C12—C11179.9 (5)C1B—C2B—C12B—C13B179.3 (5)
C1—C2—C12—C13176.3 (5)C3B—C2B—C12B—C11B178.9 (6)
C3—C2—C12—C135.1 (9)C1B—C2B—C12B—C11B2.3 (8)
C11—C12—C13—C143.3 (9)C11B—C12B—C13B—C14B1.8 (9)
C2—C12—C13—C14178.4 (6)C2B—C12B—C13B—C14B179.7 (5)
C12—C13—C14—C150.2 (11)C12B—C13B—C14B—C15B0.4 (9)
C13—C14—C15—C162.6 (10)C13B—C14B—C15B—C16B2.8 (9)
O1—C11—C16—C15179.5 (5)C14B—C15B—C16B—C11B2.7 (10)
C12—C11—C16—C151.1 (9)O1B—C11B—C16B—C15B177.6 (6)
C14—C15—C16—C112.1 (9)C12B—C11B—C16B—C15B0.2 (10)
B1—O2—C21—C2624.5 (9)B1B—O2B—C21B—C22B157.2 (6)
B1—O2—C21—C22158.6 (6)B1B—O2B—C21B—C26B21.1 (9)
C26—C21—C22—C233.7 (9)O2B—C21B—C22B—C23B177.7 (5)
O2—C21—C22—C23179.1 (5)C26B—C21B—C22B—C23B0.5 (9)
C26—C21—C22—C31175.5 (6)O2B—C21B—C22B—C31B4.8 (9)
O2—C21—C22—C311.6 (8)C26B—C21B—C22B—C31B176.9 (6)
C21—C22—C23—C245.3 (10)C21B—C22B—C23B—C24B0.5 (9)
C31—C22—C23—C24174.0 (6)C31B—C22B—C23B—C24B178.2 (5)
C22—C23—C24—C255.2 (11)C22B—C23B—C24B—C25B2.6 (9)
C23—C24—C25—C263.5 (11)C23B—C24B—C25B—C26B3.6 (10)
C24—C25—C26—C212.0 (11)C22B—C21B—C26B—C25B0.4 (9)
O2—C21—C26—C25179.0 (6)O2B—C21B—C26B—C25B178.6 (5)
C22—C21—C26—C252.2 (10)C24B—C25B—C26B—C21B2.5 (10)
C23—C22—C31—C32124.1 (7)C21B—C22B—C31B—C32B54.8 (8)
C21—C22—C31—C3255.2 (8)C23B—C22B—C31B—C32B122.7 (6)
C23—C22—C31—C3653.1 (8)C21B—C22B—C31B—C36B131.6 (6)
C21—C22—C31—C36127.7 (6)C23B—C22B—C31B—C36B50.9 (7)
C36—C31—C32—C333.3 (8)C36B—C31B—C32B—C33B1.5 (7)
C22—C31—C32—C33173.8 (5)C22B—C31B—C32B—C33B175.4 (5)
C31—C32—C33—C343.9 (8)C31B—C32B—C33B—C34B0.3 (8)
C32—C33—C34—C352.9 (9)C32B—C33B—C34B—C35B0.0 (8)
C33—C34—C35—C361.6 (8)C33B—C34B—C35B—C36B1.1 (8)
C34—C35—C36—C311.1 (7)C34B—C35B—C36B—C31B2.3 (8)
C32—C31—C36—C352.0 (8)C32B—C31B—C36B—C35B2.5 (7)
C22—C31—C36—C35175.3 (5)C22B—C31B—C36B—C35B176.3 (5)
O2A—B1A—O1A—C11A178.6 (5)O2C—B1C—O1C—C11C176.7 (5)
C1A—B1A—O1A—C11A2.9 (8)C1C—B1C—O1C—C11C1.3 (8)
O1A—B1A—O2A—C21A2.8 (10)O1C—B1C—O2C—C21C3.5 (9)
C1A—B1A—O2A—C21A178.8 (6)C1C—B1C—O2C—C21C179.0 (5)
O2A—B1A—C1A—C6A0.8 (9)O1C—B1C—C1C—C6C175.6 (5)
O1A—B1A—C1A—C6A177.7 (5)O2C—B1C—C1C—C6C8.7 (8)
O2A—B1A—C1A—C2A176.5 (5)O1C—B1C—C1C—C2C1.1 (8)
O1A—B1A—C1A—C2A5.0 (8)O2C—B1C—C1C—C2C174.6 (5)
C6A—C1A—C2A—C3A1.1 (9)C6C—C1C—C2C—C3C4.7 (8)
B1A—C1A—C2A—C3A176.3 (6)B1C—C1C—C2C—C3C178.5 (5)
C6A—C1A—C2A—C12A178.2 (5)C6C—C1C—C2C—C12C176.3 (5)
B1A—C1A—C2A—C12A4.5 (8)B1C—C1C—C2C—C12C0.6 (7)
C1A—C2A—C3A—C4A1.3 (9)C1C—C2C—C3C—C4C3.4 (9)
C12A—C2A—C3A—C4A177.9 (6)C12C—C2C—C3C—C4C177.6 (5)
C2A—C3A—C4A—C5A1.4 (10)C2C—C3C—C4C—C5C1.5 (9)
C3A—C4A—C5A—C6A4.0 (9)C3C—C4C—C5C—C6C1.1 (10)
C2A—C1A—C6A—C5A1.7 (9)C4C—C5C—C6C—C1C2.5 (10)
B1A—C1A—C6A—C5A179.0 (6)C2C—C1C—C6C—C5C4.2 (8)
C4A—C5A—C6A—C1A4.2 (9)B1C—C1C—C6C—C5C179.1 (6)
B1A—O1A—C11A—C16A179.4 (5)B1C—O1C—C11C—C16C179.1 (5)
B1A—O1A—C11A—C12A0.4 (8)B1C—O1C—C11C—C12C4.3 (9)
O1A—C11A—C12A—C13A178.8 (5)O1C—C11C—C12C—C13C179.1 (5)
C16A—C11A—C12A—C13A2.2 (8)C16C—C11C—C12C—C13C2.6 (9)
O1A—C11A—C12A—C2A0.2 (8)O1C—C11C—C12C—C2C4.7 (8)
C16A—C11A—C12A—C2A178.8 (5)C16C—C11C—C12C—C2C178.8 (6)
C1A—C2A—C12A—C11A2.0 (8)C3C—C2C—C12C—C13C2.8 (9)
C3A—C2A—C12A—C11A178.7 (6)C1C—C2C—C12C—C13C178.2 (6)
C1A—C2A—C12A—C13A179.1 (5)C3C—C2C—C12C—C11C178.8 (5)
C3A—C2A—C12A—C13A0.1 (9)C1C—C2C—C12C—C11C2.1 (8)
C11A—C12A—C13A—C14A2.0 (8)C11C—C12C—C13C—C14C2.6 (9)
C2A—C12A—C13A—C14A179.1 (6)C2C—C12C—C13C—C14C178.7 (5)
C12A—C13A—C14A—C15A0.0 (10)C12C—C13C—C14C—C15C0.4 (9)
C13A—C14A—C15A—C16A1.9 (10)C13C—C14C—C15C—C16C2.0 (9)
O1A—C11A—C16A—C15A179.5 (5)C14C—C15C—C16C—C11C2.1 (10)
C12A—C11A—C16A—C15A0.5 (9)O1C—C11C—C16C—C15C177.0 (6)
C14A—C15A—C16A—C11A1.6 (9)C12C—C11C—C16C—C15C0.3 (10)
B1A—O2A—C21A—C26A15.5 (10)B1C—O2C—C21C—C22C173.2 (6)
B1A—O2A—C21A—C22A169.6 (6)B1C—O2C—C21C—C26C7.9 (9)
C26A—C21A—C22A—C23A0.8 (9)O2C—C21C—C22C—C23C179.0 (5)
O2A—C21A—C22A—C23A174.4 (5)C26C—C21C—C22C—C23C0.2 (9)
C26A—C21A—C22A—C31A178.0 (5)O2C—C21C—C22C—C31C3.6 (9)
O2A—C21A—C22A—C31A2.8 (8)C26C—C21C—C22C—C31C177.6 (6)
C21A—C22A—C23A—C24A2.5 (8)C21C—C22C—C23C—C24C0.6 (9)
C31A—C22A—C23A—C24A179.8 (5)C31C—C22C—C23C—C24C177.0 (6)
C22A—C23A—C24A—C25A2.8 (9)C22C—C23C—C24C—C25C0.5 (11)
C23A—C24A—C25A—C26A1.3 (10)C23C—C24C—C25C—C26C0.4 (11)
C24A—C25A—C26A—C21A0.5 (11)C22C—C21C—C26C—C25C1.0 (10)
O2A—C21A—C26A—C25A175.4 (6)O2C—C21C—C26C—C25C179.8 (5)
C22A—C21A—C26A—C25A0.7 (10)C24C—C25C—C26C—C21C1.1 (10)
C23A—C22A—C31A—C36A40.0 (8)C21C—C22C—C31C—C32C42.2 (9)
C21A—C22A—C31A—C36A137.2 (6)C23C—C22C—C31C—C32C135.2 (6)
C23A—C22A—C31A—C32A135.8 (6)C21C—C22C—C31C—C36C135.1 (6)
C21A—C22A—C31A—C32A47.0 (8)C23C—C22C—C31C—C36C47.5 (8)
C36A—C31A—C32A—C33A1.6 (8)C36C—C31C—C32C—C33C3.6 (9)
C22A—C31A—C32A—C33A174.3 (5)C22C—C31C—C32C—C33C179.1 (5)
C31A—C32A—C33A—C34A1.5 (8)C31C—C32C—C33C—C34C0.3 (9)
C32A—C33A—C34A—C35A0.0 (10)C32C—C33C—C34C—C35C3.4 (11)
C33A—C34A—C35A—C36A1.4 (11)C33C—C34C—C35C—C36C3.6 (12)
C32A—C31A—C36A—C35A0.2 (9)C34C—C35C—C36C—C31C0.2 (10)
C22A—C31A—C36A—C35A175.7 (6)C32C—C31C—C36C—C35C3.4 (9)
C34A—C35A—C36A—C31A1.3 (10)C22C—C31C—C36C—C35C179.2 (6)
Comparative table of dihedral angles (°) in the four molecules in the asymmetric unit of (Vb). DA1 is the dihedral angle between the 10-oxa-9-boraphenanthrene moiety and the phenyl ring attached to the O atom, and DA2 is the dihedral angle between the two rings of the biphenyl residue. top
MoleculeDA1DA2
120.4 (3)55.17 (16)
A11.4 (3)44.3 (2)
B22.5 (2)53.44 (15)
C10.8 (3)45.4 (2)
 

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